Dimethylformamide → 6-fluoro-2-pyridin-3-yl-1H-indole-3-carbonitrile

HRID 1630868Notes

Reaction equation

HRID 1630868 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:8]2)=[CH:4][CH:3]=1.ClS([N:21]=[C:22]=O)(=O)=O.CN(C=O)C>ClCCl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:22]#[N:21])=[C:7]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 582155816-fluoro-2-pyridin-3-yl-1H-indole

Product 1

HCID 582158106-fluoro-2-pyridin-3-yl-1H-indole-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-fluoro-2-pyridin-3-yl-1H-indole (Example 89, 212 mg, 1.0 mmol) in dichloromethane (90 mL) at ambient temperature is added chlorosulfonyl isocyanate (0.71 g, 5 mmol) and the mixture is stirred overnight. Anhydrous DMF (1 mL) is added. After 1 h, the solvent is removed in vacuo and the residue purified by HPLC using an Xbridge C18 with a gradient of acetonitrile in 0.1% NH4OH to give 6-fluoro-2-pyridin-3-yl-1H-indole-3-carbonitrile as a white solid. 1H NMR (400 MHz, DMSO-d6) d ppm 7.12-7.21 (m, 1H), 7.39 (dd, J=9.5, 2.4 Hz, 1H), 7.64-7.74 (m, 2H), 8.27-8.35 (m, 1H), 8.73 (dd, J=4.9, 1.6 Hz, 1H), 9.14 (d, J=1.8 Hz, 1H), 12.89 (s, 1H). MS (ESI) m/z 238.0 (M+H)+.

Workup

  1. waitAfter 1 h
  2. customthe solvent is removed in vacuo
  3. customthe residue purified by HPLC

Sources & evidence

ORD record
ord-e6273e677fc34b54b98074b3d319076b
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

Loading…