Acetonitrile → 5-chloro-2-pyridin-3-yl-1H-indole-3-carbonitrile

HRID 593600Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[CH:5]2.[C:17](#[N:19])C>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[C:5]2[C:17]#[N:19]

Participants

Reactant 2

HCID 6342Acetonitrile

HCID 12011262HCID 12011262, compound

Product 1

HCID 582158075-chloro-2-pyridin-3-yl-1H-indole-3-carbonitrile

Procedure

5-Chloro-2-pyridin-3-yl-1H-indole (Example 87) is processed according to the method described in Example 140, using acetonitrile instead of dichloromethane, to give 5-chloro-2-pyridin-3-yl-1H-indole-3-carbonitrile. 1H NMR (400 MHz, MeOD) δ ppm 7.36 (dd, J=8.6, 2.0 Hz, 1H), 7.57 (d, J=8.6 Hz, 1H), 7.65-7.77 (m, 2H), 8.43 (dt, J=8.1, 2.0 Hz, 1H), 8.72 (d, J=4.8 Hz, 1H), 9.16 (s, 1H). HRMS (ESI) m/z 254.0495 [(M+H)+ calcd for C14H9ClN3: 254.0485].

Sources & evidence

ORD record: ord-c66cba686ce641dea59f7b61077c466f
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242963B2

Reaction notes

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