Hydrazine → HCID 135584186, compound

HRID 33337Notes

Reaction equation

C[O:2][C:3]([C:5]1[C:6]2[C:7]([CH:21]=O)=[C:8]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[NH:9][C:10]=2[CH:11]=[CH:12][CH:13]=1)=O.[NH2:23][NH2:24]>>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:8]2[NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[C:5]4[C:3](=[O:2])[NH:24][N:23]=[CH:21][C:7]=2[C:6]=34)=[CH:15][CH:16]=1

Participants

Reactant 2

HCID 9321Hydrazine

HCID 544772522-(4-fluoro-phenyl)-3-formyl-1H-indole-4-carboxylic acid methyl ester

Product 1

HCID 135584186HCID 135584186, compound

Procedure

In a manner similar to that described for Example ZZZ, 2-(4-fluoro-phenyl)-3-formyl-1H-indole-4-carboxylic acid methyl ester (145 mg, 0.49 mmol) was condensed with hydrazine (45 mg, 1.41 mmol) to give 2-(4-fluoro-phenyl)-1,5-dihydro-[1,2]diazepino[4,5,6-cd]indol-6-one, 120 mg (88%) as a bright yellow solid: m.p. 340-341° C. (dec); 1H NMR (300 MHz, d6-DMSO) δ 7.22 (app t, J=7.8 Hz 1H), 7.43 (m, 3H), 7.54 (m, 2H), 7.73 (m, 2H), 10.33 (s, 1H), 12.23 (br s, 1H). MS (electrospray, MH+) 280. Anal. (C16H10FN3O) C, H, N.

Sources & evidence

ORD record: ord-a59eb7894f9340008543fe76dffa8a00
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429578B2

Reaction notes

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