6-Chloro-3-pyridinecarbonitrile → HCID 135421278, compound

HRID 2245571Notes

Reaction equation

HRID 2245571 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11]2)=[O:7].[Cl:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][N:20]=1>>[ClH:18].[C:23]([C:22]1[CH:25]=[CH:26][C:19]([C:11]2[C:10]3[C:14](=[CH:15][CH:16]=[C:8]([C:6]([NH:5][CH2:4][CH2:3][O:2][CH3:1])=[O:7])[CH:9]=3)[NH:13][C:12]=2[OH:17])=[N:20][CH:21]=1)#[N:24]

Participants

3

Reactant 2

HCID 51520946-Chloro-3-pyridinecarbonitrileHCID 68544478HCID 68544478, compound

Product 1

HCID 135421278HCID 135421278, compoundYield 28%

Procedure

Starting materials: N-(2-methoxyethyl)-2-oxoindoline-5-carboxamide and 6-chloronicotinonitrile. The residue was purified on a silica gel column using a gradient chloroform/methanol, (100:1 to 10:1), as the eluent. Yield: 28% of the title compound: 1H NMR (DMSO-d6, 400 MHz) δ 10.89 (s, 1H), 8.56 (m, 1H), 8.49 (m, 1H), 7.98 (s, 1H), 7.85 (dd, J=10, 2 Hz, 1H), 7.70 (d, J=10 Hz, 1H), 7.59 (dd, J=9, 2 Hz, 1H) 6.96 (d, J=9 Hz, 1H), 3.45 (m, 4H), 3.27 (s, 3H); MS (ES) m/z 337 (M++1).

Workup

  1. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-e0751d53b8184928b99a9d22eae3e743
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

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