6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine → HCID 11418401, compound

HRID 898332Notes

Reaction equation

HRID 898332 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.[F:16][C:17]([F:26])([F:25])[C:18]1[CH:19]=[CH:20][C:21](Br)=[N:22][CH:23]=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:21]3[CH:20]=[CH:19][C:18]([C:17]([F:26])([F:25])[F:16])=[CH:23][N:22]=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 27364342-Bromo-5-(trifluoromethyl)pyridine

Product 1

HCID 11418401HCID 11418401, compound

Procedure

6-Bromo-N-[5-(trifluoromethyl)pyridin-2-yl]-2,3,4,9-tetrahydro-1H-carbazol-1-amine was prepared from 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine (75 mg, 0.28 mmol) and 5-(trifluoromethyl)-2-bromopyridine (192 mg, 0.85 mmol) in a similar manner as described in Example 22 to give 6.5 mg (6%) of a off-white solid. 1H-NMR (DMSO-d6): δ 10.95 (s, 1H), 8.36 (s, 1H), 7.79 (d, 1H), 7.64 (dd, 1H), 7.57 (s, 1H), 7.23 (d, 1H), 7.13 (dd, 1H), 6.62 (d, 1H), 5.40-5.36 (m, 1H), 2.70-2.55 (m, 2H), 2.06-1.78 (m, 4H); MS m/z (M−1) 408, 410.

Sources & evidence

ORD record
ord-411bfcfd8cbd4976874d4f4bb75ed2e8
Source dataset
uspto-grants-2008_04
Patent number
US07351733B2

Reaction notes

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