upekkha also means indifference, boredom in some contexts. How does boredom lead to awakening?

 

🛆👁 Upekkha = equanimous-observation

1. as awakening factor 7🛆👁 : doing vipassana to awaken (SN ^46.3), is exactly the same as (#2) upekkha in 4 jhānas.
2. in four jhānas (4j🌕 ) doing vipassana (AN ^3.102).
3. in 5👑abi️ as in MN ¹⁵², one can infer, is also the same as the above,
since for one to be an awakened noble, one would need a minimum of first jhāna, obtained via 7sb☀️ .
4. in brahma-vihāra 4bv☮️ , for an ariya, would share attributes with all of the above.
As part of 4bv, one would energetically pervade in all directions (of desired radius).
upekkha that could be sensed by other beings as a palpable peaceful radiation,
similar to how seeing someone smile can make you smile.
5. upekkha of 5 indriya/vedana (SN ^48.37) corresponds to 3rd and 4th jhāna.
The 4 jhānas are the progressive pacification (passaddhi-sambojjhanga)
of these 5 indriya/vedana (SN ^36.11).
6. Upekkha of unawakened ordinary person = equanimous-boredom when indulging in 5kg , see MN ^137.3.5 and SN ^36.31.3.1.

⛔ Upekkha is not just 'equanimity'. It's equanimous-observation. Upekkha = upa + ikkhati (👁 looking upon [with right view]).
Just as a peanut butter sandwich is not a peanut butter AND JELLY sandwich. Two different things.
✅ Upekkha has an equanimity aspect, but more importantly, vipassana capability to realize awakening.
It's basically Dhamma-vicaya-bojjhanga supercharged with samādhi-sam-bojjhanga (aka four jhānas) + right view.

These two suttas show the context for boredom

6. Upekkha of unawakened ordinary person = equanimous-boredom when indulging in 5kg , see MN ^137.3.5 and SN ^36.31.3.1.

AFAIK, most if not all other translators still translate upekkha as 'equanimity' in that context.

B. Bodhi for example:

14. “Herein, what are the six kinds of equanimity based on the household life?
On seeing a form with the eye, equanimity arises in a foolish infatuated ordinary person, in an untaught ordinary person who has not conquered his limitations or conquered the results [of action] and who is blind to danger.
Such equanimity as this does not transcend the form;
that is why it is called equanimity based on the household life.

Since upekkha is a factor of awakening, the 7th out of 7 awakening factors, 

I felt it was necessary to make the distinction clear between upekkha of jhānas and bojjhanga, 

and the upekkha of a wordling indulging in sensual pleasures like food and sex and getting temporary boredom from it. 

Upekkha of worldling temporarily disinterested in sex = equanimous-boredom.

Upekkha of disciple striving for arahantship = equanimous-observation

the 'observation'  leads to awakening!

equanimity only lands you rebirth in the brahma realms.

That's why it's called 7 factors of awakening, 

not 7 factors of  indifference,

nor 7 factors that lead to Brahma realm rebirth.