6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine → HCID 11245553, compound

HRID 898333Notes

Reaction equation

HRID 898333 reaction equation
[Br: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.Cl[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][N:18]=1>>[Br: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:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][N:18]=3)[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

3

Reactant 2

HCID 5978796-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amineHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 11245553HCID 11245553, compound

Procedure

6-[(6-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)amino]nicotinonitrile was prepared from 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine (75 mg, 0.28 mmol) and 6-chloronicotinonitrile (118 mg, 0.85 mmol) in a similar manner as described in Example 22 to give 6.5 mg (6%) of a light brown solid. 1H-NMR (DMSO-d6): δ 10.95 (s, 1H), 8.36 (s, 1H), 7.79 (d, 1H), 7.64 (dd, 1H), 7.57 (d, 1H), 7.23 (d, 1H), 7.13 (dd, 1H), 6.62 (d, 1H), 5.40-5.35 (m, 1H), 2.70-2.55 (m, 2H), 2.07-1.78 (m, 4H); MS m/z (M−1) 365, 367.

Sources & evidence

ORD record
ord-12736a1eebf84573b38d5d5dfe361f96
Source dataset
uspto-grants-2008_04
Patent number
US07351733B2

Reaction notes

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