Benzyl chloroformate → Benzyl N-(6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)carbamate

HRID 28684Notes

Reaction equation

HRID 28684 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]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>>[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](=[O:18])[O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

3

Reactant 2

HCID 10387Benzyl chloroformateHCID 5978796-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine

Product 1

HCID 11315519Benzyl N-(6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-yl)carbamate

Procedure

Benzyl 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-ylcarbamate was prepared from 6-bromo-2,3,4,9-tetrahydro-1H-carbazol-1-amine and benzyl chloroformate in a similar manner as described above to give a white solid (16% yield). 1H-NMR (CDCl3): δ 8.69 (s, 1H), 7.60 (s, 1H), 7.43-7.31 (m, 5H), 7.27-7.21 (m, 1H), 7.17 (d, 1H), 5.16 (q, 2H), 5.08 (m, 1H), 4.92 (m, 1H), 2.66 (m, 2H), 2.20 (m, 1H), 1.89 (m, 2H), 1.80 (m, 1H); MS m/z 400 (M+1).

Sources & evidence

ORD record
ord-aa97c43076864603881da649040b1485
Source dataset
uspto-grants-2008_09
Patent number
US07419997B2

Reaction notes

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