6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine → HCID 11452625, compound

HRID 898331Notes

Reaction equation

HRID 898331 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[N:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[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[N:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[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 133170192-Chloro-5-(trifluoromethyl)pyrimidine

Product 1

HCID 11452625HCID 11452625, compound

Procedure

6-Bromo-N-[5-(trifluoromethyl)pyrimidin-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 2-chloro-5-(trifluoromethyl)-pyrimidine (0.5 mL) in a similar manner as described in Example 22 to give 5 mg (4%) of a yellow solid. 1H-NMR (DMSO-d6) taken at 80° C.: δ 10.94-10.88 (m, 1H), 8.69-8.62 (m, 1H), 8.30-8.24 (m, 1H), 7.55 (s, 1H), 7.21 (d, 1H), 7.13-7.10 (m, 1H), 7.02 (d, 1H), 5.40-5.27 (m, 1H), 2.62-2.58 (m, 2H), 2.08-1.96 (m, 2H), 1.87-1.76 (m, 2H); MS m/z (M−1) 409, 411.

Sources & evidence

ORD record
ord-9594617a2f7a4f7da87656c37c79faa6
Source dataset
uspto-grants-2008_04
Patent number
US07351733B2

Reaction notes

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