Acetonitrile → 2-pyridin-3-yl-1H-indole-3,5-dicarbonitrile

HRID 1630869Notes

Reaction equation

HRID 1630869 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([C:16]#[N:17])=[CH:11][CH:10]=3)[CH:2]=1.[C:18](#[N:20])C>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[NH:8][C:9]3[C:14]([C:15]=2[C:18]#[N:20])=[CH:13][C:12]([C:16]#[N:17])=[CH:11][CH:10]=3)[CH:2]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 445541352-pyridin-3-yl-1H-indole-5-carbonitrile

Product 1

HCID 582157622-pyridin-3-yl-1H-indole-3,5-dicarbonitrile

Procedure

2-Pyridin-3-yl-1H-indole-5-carbonitrile (Example 8) is processed according to the method described in Example 140, using acetonitrile instead of dichloromethane, to give 2-pyridin-3-yl-1H-indole-3,5-dicarbonitrile. 1H NMR (400 MHz, MeOD) δ ppm 7.68 (dd, J=8.6 Hz, 1H), 7.72 (dd, J=8.1, 4.8 Hz, 1H), 7.75 (d, J=8.3 Hz, 1H), 8.17 (s, 1H), 8.47 (dt, J=8.1, 1.9 Hz, 1H), 8.76 (dd, J=4.8, 1.5 Hz, 1H), 9.19 (d, J=1.5 Hz, 1H). HRMS (ESI) m/z 245.0823 [(M+H)+ calcd for C15H9N4: 245.0827].

Sources & evidence

ORD record
ord-13259c7ce0284eb7b0cd199a0d3807ef
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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