Water → HCID 90037382, compound

HRID 1055412Notes

Reaction equation

[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]#[N:12].F[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[C:16]#[N:17].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[C:16]([C:15]1[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=1[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([CH3:1])=[C:3]1[C:11]#[N:12])#[N:17]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 3-methyl-1H-indole-2-carbonitrile (500 mg, 3.2 mmol), 2-fluorobenzonitrile (388 mg, 3.2 mmol) and Cs2CO3 (1.05 g, 3.2 mmol) in DMF (10 mL) was heated at 60° C. overnight. The mixture was poured into H2O and a precipitate formed. The solid was collected by filtration, washed with H2O and hexane, and dried under vacuum to give 1-(2-cyanophenyl)-3-methyl-1H-indole-2-carbonitrile (780 mg, 94.6%) as an off white solid that was used without purification.

Workup

customa precipitate formed
filtrationThe solid was collected by filtration
washwashed with H2O and hexane
customdried under vacuum

Sources & evidence

ORD record: ord-64051bb5bd894dc69ab7f1c804b95350
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394263B2

Reaction notes

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