Sodium Cyanide → (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-N-methyl-acetamide

HRID 602762Notes

Reaction equation

CO[C:3](=[O:29])[C:4]([S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21])([CH:6]1[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[CH:14]=3)[NH:9][C:8]=2[CH2:7]1)[F:5].[C-:30]#[N:31].[Na+]>CN>[C:23]1([S:20]([C:4]([CH:6]2[CH2:18][CH2:17][C:16]3[C:15]4[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[CH:14]=4)[NH:9][C:8]=3[CH2:7]2)([F:5])[C:3]([NH:31][CH3:30])=[O:29])(=[O:21])=[O:22])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To 400 mg (0.92 mmol) of (RS,SR)-benzenesulfonyl-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-fluoro-acetic acid methyl ester (from example 12) in a sealed tube were added 20 mL of methylamine (33% wt. solution in EtOH) and 13 mg (0.27 mmol, 0.3 eq) of sodium cyanide. The reaction mixture was stirred at 90° C. for 2 hours, and the solvent was evaporated. Column chromatography on silica gel with EtOAc yielded 340 mg (86%) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-2-fluoro-N-methyl-acetamide as a white solid, MS: 435 (MH+).

Workup

customthe solvent was evaporated

Sources & evidence

ORD record: ord-b0864ed6befc4534a311dc51d3736be2
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906546B2

Reaction notes

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