Quinoxaline-6-carboxaldehyde → HCID 71268679, compound

HRID 929363Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[F:8].[Li]CCCC.[N:21]1[C:30]2[C:25](=[CH:26][C:27]([CH:31]=[O:32])=[CH:28][CH:29]=2)[N:24]=[CH:23][CH:22]=1>C1COCC1>[F:8][C:7]1[CH:6]=[CH:5][C:4]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:3][C:2]=1[CH:31]([OH:32])[C:27]1[CH:26]=[C:25]2[C:30](=[CH:29][CH:28]=1)[N:21]=[CH:22][CH:23]=[N:24]2

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of N-(3-bromo-4-fluorophenyl)pivalamide (9.48 g, 34.6 mmol, 1.2 eq.) in THF (100 mL) cooled at −78° C. was added n-BuLi (27.6 mL, 69 mmol, 2.4 eq.) dropwise. The resulting mixture was stirred at −78° C. for 1 h, then was added a solution of quinoxaline-6-carbaldehyde (4.5 g, 28.8 mmol, 1.0 eq.) in THF (200 mL) dropwise. The mixture was stirred at −78° C. for 1 h, then quenched by the addition of NH4Cl solution. The mixture was extracted with EA (100 mL ×3) and the combined organic layers were dried over Na2SO4 and concentrated. The resulting residue was purified by flash column chromatography (PE/EA=1/1, v/v) to afford N-(4-fluoro-3-(hydroxy(quinoxalin-6-yl)methyl)phenyl)pivalamide as a yellow foam (5.16 g, 50.7%).

Workup

stirringThe mixture was stirred at −78° C. for 1 h
customquenched by the addition of NH4Cl solution
extractionThe mixture was extracted with EA (100 mL ×3)
dry with materialthe combined organic layers were dried over Na2SO4
concentrationconcentrated
customThe resulting residue was purified by flash column chromatography (PE/EA=1/1

Sources & evidence

ORD record: ord-3d58d8f79e304ae4aec1431640e1510d
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09295671B2

Reaction notes

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