Ammonium Hydroxide → HCID 86611322, compound

HRID 2235094Notes

Reaction equation

C([BH3-])#N.[Na+].[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH:24]=[C:23]3[C:19]([CH:20]=[CH:21][NH:22]3)=[CH:18][CH:17]=2)=[O:15])=[CH:9][C:8]=1[C:25]([F:28])([F:27])[F:26])#[N:6].[OH-].[NH4+]>C(O)(=O)C.O.ClCCl>[C:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH:24]=[C:23]3[C:19]([CH2:20][CH2:21][NH:22]3)=[CH:18][CH:17]=2)=[O:15])=[CH:9][C:8]=1[C:25]([F:28])([F:26])[F:27])#[N:6]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium cyanoborohydride (4.6 g, 73.8 mmol, 3 equiv.) was carefully added to a stirred solution of 1H-indole-6-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide (2.4 g, 7.38 mmol, 1 equiv.) in acetic acid (25 mL) over 5 minutes at room temperature. The reaction mixture was stirred for 30 minutes then cooled down to 0° C. and slowly poured onto concentrated ammonium hydroxide (78 mL, d=0.880) at 0° C. The mixture was diluted with water (25 mL) and dichloromethane (25 mL), the organic layer was separated and the aqueous layer was extracted with dichloromethane (2×25 mL). The organic layers were combined, dried over Na2SO4 and the solvent was removed under vacuum to afford crude 2,3-dihydro-1H-indole-6-carboxylic acid (4-cyano-3-trifluoromethyl-phenyl)-amide, 1.8 g (73% yield), this material was taken onto the next step without further purification. LC @215 nm; Rt 1.13: 80%, m/z (ES+): 372 (M+H+MeCN).

Workup

customthe organic layer was separated
extractionthe aqueous layer was extracted with dichloromethane (2×25 mL)
dry with materialdried over Na2SO4
customthe solvent was removed under vacuum

Sources & evidence

ORD record: ord-b171d1c7682249809edd9c3416b2f752
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713996B2

Reaction notes

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