Sodium borohydride → HCID 86281901, compound

HRID 1052974Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[C:10]3([CH2:23][C:24](OC)=[O:25])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:5]([CH3:28])[O:4][N:3]=1.[BH4-].[Na+]>CCO>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[C:10]3([CH2:23][CH2:24][OH:25])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:5]([CH3:28])[O:4][N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 2-(5-(3,5-dimethylisoxazol-4-yl)-2-oxo-3-phenylindolin-3-yl)acetate (50 mg, 0.13 mmol) in EtOH (20 mL) was added NaBH4 (49 mg, 1.3 mmol), the reaction mixture was stirred at reflux for 3.0 h. After cooling to 0° C., the reaction was quenched by addition of aq. saturated NH4Cl (2 mL) solution. The mixture was diluted with water (10 mL) and extracted with EtOAc (15 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo to yield crude product which were purified on flash column chromatography to afford the title compound as a white solid (10 mg, 22%). 1H NMR (400 MHz, DMSO-d6): δH 10.59 (s, 1H), 7.22-7.35 (m, 7H), 6.98 (d, J=8.0 Hz, 1H), 4.48-4.51 (m, 1H), 3.15-3.17 (m, 2H), 2.44-2.48 (m, 2H), 2.32 (s, 3H), 2.20 (s, 3H). MS (ESI) m/e [M+1]+ 349.

Workup

temperatureat reflux for 3.0 h
customthe reaction was quenched by addition of aq. saturated NH4Cl (2 mL) solution
additionThe mixture was diluted with water (10 mL)
extractionextracted with EtOAc (15 mL)
washThe organic layer was washed with brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
customevaporated in vacuo
customto yield crude product which
customwere purified on flash column chromatography

Sources & evidence

ORD record: ord-8921f28a853b401c9b534a251eb0a25a
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09393232B2

Reaction notes

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