N-(2-bromo-4-fluorophenyl)acetamide → HCID 22266714, compound

HRID 489548Notes

Reaction equation

HRID 489548 reaction equation
C(N(CC)CCC1C=CC([C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[C:18]4[C:24](=[O:25])[NH:23][CH2:22][CH2:21][C:20]=2[C:19]=34)=CC=1)C.Br[C:29]1[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=1[NH:36][C:37](=[O:39])[CH3:38]>>[F:35][C:33]1[CH:32]=[CH:31][C:30]([NH:36][C:37](=[O:39])[CH3:38])=[C:29]([C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[C:18]4[C:24](=[O:25])[NH:23][CH2:22][CH2:21][C:20]=2[C:19]=34)[CH:34]=1

Participants

3

Reactant 2

HCID 688184N-(2-bromo-4-fluorophenyl)acetamideHCID 222666792-[4-(2-Diethylamino-ethyl)-phenyl]-3,4,5,6-tetrahydro-azepino[5,4,3-cd]indol-6-one

Product 1

HCID 22266714HCID 22266714, compound

Procedure

In a manner similar to that described for 2-[4-(2-diethylamino-ethyl)-phenyl]-3,4,5,6-tetrahydro-azepino[5,4,3-cd]indol-6-one (Example YY), the tricyclic bromide (300 mg, 1.13 mmol) and N-(2-bromo-4-fluoro-phenyl)-acetamide (276 mg, 1.19 mmol) were coupled to yield N-[4-fluoro-2-(6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-2-yl)-phenyl]-acetamide, 83 mg (22%) as a beige solid: m.p. 260-261° C. (dec); 1H NMR (300 MHz, d6-DMSO) δ 1.97 (s, 3H), 2.66 (m, 2H), 3.33 (m, 2H), 7.25 (m, 3H), 7.56 (dd, J=7.5, 0.6 Hz, 1H), 7.70 (dd, J=7.2, 0.6 Hz, 1H), 7.76 (m, 1H), 8.04 (br t, 1H), 11.50 (br s, 1H). MS (FAB, MH+): 338. Anal. (C16H19FN3O2.0.16 H2O) C, H, N.

Sources & evidence

ORD record
ord-315f328cec26420d837efff544b57422
Source dataset
uspto-grants-2005_12
Patent number
US06977298B2

Reaction notes

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