Sodium borohydride → 2'-Hydroxymethyl-biphenyl-4-carboxylic acid quinolin-7-ylamide

HRID 1984977Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[CH:26]=[O:27])=[CH:16][CH:15]=3)=[O:13])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO.CCOC(C)=O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[CH2:26][OH:27])=[CH:16][CH:15]=3)=[O:13])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2′-formyl-biphenyl-4-carboxylic acid quinolin-7-ylamide, Example 28, (90 mg, 0.25 mmol) in MeOH (2 mL) was added sodium borohydride (20 mg, 0.51 mmol) and the mixture was stirred for 10 min at 0° C. The reaction mixture was diluted with EtOAc (50 mL) and washed with satd NH4Cl (5 mL). The EtOAc layer was separated, washed with brine, dried over MgSO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (gradient, 40 to 90% EtOAc/hexane) to provide the title compound as a yellow amorphous solid. MS (ESI, pos. ion.) m/z: 355 (M+1).

Workup

washwashed with satd NH4Cl (5 mL)
customThe EtOAc layer was separated
washwashed with brine
dry with materialdried over MgSO4
filtrationfiltered
customThe filtrate was evaporated in vacuo
customthe residue was purified by silica gel column chromatography (gradient, 40 to 90% EtOAc/hexane)

Sources & evidence

ORD record: ord-09922cbba4d34db992f2a2c23f733b15
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544803B2

Reaction notes

Loading…