2-Phenyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-9-one → 2-[3-(4-Fluoro-phenoxy)-phenyl]-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one

HRID 33311Notes

Reaction equation

HRID 33311 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]4[C:19](=[O:20])[NH:18][CH2:17][CH2:16][C:15]=2[C:14]=34)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:21][C:22]1[CH:37]=[CH:36][C:25]([O:26]C2C=C(B(O)O)C=CC=2)=[CH:24][CH:23]=1>>[F:21][C:22]1[CH:37]=[CH:36][C:25]([O:26][C:5]2[CH:6]=[C:1]([C:7]3[NH:8][C:9]4[CH:10]=[CH:11][CH:12]=[C:13]5[C:19](=[O:20])[NH:18][CH2:17][CH2:16][C:15]=3[C:14]=45)[CH:2]=[CH:3][CH:4]=2)=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 102208822-Phenyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-9-oneHCID 222667133-(4-Fluorophenoxy)phenylboronic acid

Product 1

HCID 222667062-[3-(4-Fluoro-phenoxy)-phenyl]-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one

Procedure

In a manner similar to that described for Compound 12, the tricyclic bromide (200 mg, 0.75 mmol) and 3-(4-fluoro-phenoxy)-phenylboronic acid (213 mg, 0.83 mmol) were coupled to yield 2-[3-(4-fluoro-phenoxy)-phenyl]-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one, 170 mg (60%) as a yellow crystalline solid: m.p. 240-241° C.; 1H NMR (300 MHz, d6-DMSO) δ 3.01 (m, 2H), 3.38 (m, 2H), 6.99 (m, 2H), 7.21 (m, 6H), 7.42 (m, 1H), 7.54 (m, 2H), 7.68 (m, 1H), 8.09 (br t, 1H), 11.60 (br s, 1H). MS (FAB, MH+) 373. Anal. (C23H17N2O2F.0.5 H2O) C, H, N.

Sources & evidence

ORD record
ord-d38067ef64fe4b458787abc9d2b2927f
Source dataset
uspto-grants-2008_09
Patent number
US07429578B2

Reaction notes

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