5-Aminoindole → HCID 11485793, compound

HRID 898341Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9](=O)[CH2:8][CH2:7][CH2:6][C:5]2=1.[NH2:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2>>[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:16][C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][CH:21]=[CH:20]4)[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

Reactant 2

HCID 788675-Aminoindole

HCID 7085296-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one

Product 1

HCID 11485793HCID 11485793, compound

Procedure

6-Bromo-N-(1H-indol-5-yl)-2,3,4,9-tetrahydro-1H-carbazol-1-amine was prepared from 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one (100 mg, 0.76 mmol) and 5-aminoindole (100 mg, 0.76 mmol) in a similar manner as described above to give 54 mg (37%) of a white solid; 1H-NMR (DMSO-d6): δ 11.08 (s, 1H), 10.61 (s, 1H), 7.55 (d, 1H), 7.23 (d, 1H), 7.14-7.11 (m, 2H), 7.10 (d, 1H), 6.84-6.83 (m, 1H), 6.65 (dd, 1H), 6.18-6.17 (m, 1H), 5.21 (d, 1H), 4.77-4.71 (m, 1H), 2.68-2.54 (m, 2H), 2.02-1.89 (m, 2H), 1.84-1.73 (m, 2H); MS m/z (M+1) 378, 380.

Sources & evidence

ORD record: ord-6bb5dda6322b4649a8e816168d9cb4c5
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351733B2

Reaction notes

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