Pyridine-2-carbonyl chloride → N-(6-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl)picolinamide

HRID 28707

Reaction equation

HRID 28707 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH2:15])[CH2:8][CH2:7][CH2:6][C:5]2=1.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](Cl)=[O:23]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([NH:15][C:22]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=3)=[O:23])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

3

Reactant 2

HCID 135034Pyridine-2-carbonyl chlorideHCID 177434976-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine

Product 1

HCID 11438772N-(6-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl)picolinamide

Procedure

N-(6-Chloro-2,3,4,9-tetrahydro-1H-carbazol-1-yl)-2-pyridinecarboxamide was prepared from 6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine and picolinoyl chloride in a similar manner as described in Example 14 to give an off-white solid (62% yield). 1H-NMR (DMSO-d6): δ 10.93 (s, 1H), 8.78 (d, 1H), 8.61 (m, 1H), 8.12 (m, 1H), 8.02 (m, 1H), 7.61 (m, 1H), 7.43 (m, 1H), 7.26 (d, 1H), 7.01 (dd, 1H), 5.34 (m, 1H), 2.64 (m, 2H), 2.00 (m, 3H), 1.82 (m, 1H); MS m/z 348 (M+Na).

Sources & evidence

ORD record
ord-3e3e85cb1abb48dcb6de7856e758b210
Source dataset
uspto-grants-2008_09
Patent number
US07419997B2

Linked notes

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