Methanol → Ethyl 7-(2-bromo-3-chloro-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

HRID 517930Notes

Reaction equation

BrC1N=C2CCCN(CCCCCCC([O-])=O)C2=NC=1Cl.[Br:22][C:23]1[N:24]=[C:25]2[CH2:33][CH2:32][C:31](=O)[N:30]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:26]2=[N:27][C:28]=1[Cl:29].CO>C1COCC1>[Br:22][C:23]1[N:24]=[C:25]2[CH2:33][CH2:32][CH2:31][N:30]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:26]2=[N:27][C:28]=1[Cl:29]

Participants

Conditions

Temperature: 0 °C

Procedure

7-(2-bromo-3-chloro-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate A cooled (0° C.) solution of ethyl 7-(2-bromo-3-chloro-6-oxo-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate (step 1)(1.0 g, 2.388 mmol) in THF (10 ml) under a nitrogen atmosphere was treated with borane-methyl sulfide complex over 30 mins. The resulting mixture was stirred at 0° C. for 2 h 30 minutes and stored in a fridge overnight. The mixture was cooled in an ice bath and cautiously treated with MeOH (5 ml). The yellow solution was stirred at 0° C. for 1 hour and concentrated under reduced pressure. The crude material was purified by chromatography on silica eluting with 0-100% EtOAc in iso-hexane to afford ethyl 7-(2-bromo-3-chloro-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)heptanoate

Workup

additionwas treated with borane-methyl sulfide complex over 30 mins
waitstored in a fridge overnight
temperatureThe mixture was cooled in an ice bath
stirringThe yellow solution was stirred at 0° C. for 1 hour
concentrationconcentrated under reduced pressure
customThe crude material was purified by chromatography on silica eluting with 0-100% EtOAc in iso-hexane

Sources & evidence

ORD record: ord-95d6debe8bb54b95a452d5ab7b8c4be5
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115129B2

Reaction notes

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