Pyrrolidine → 8-Fluoro-2-(4-pyrrolidin-1-ylmethyl-phenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one

HRID 2298949Notes

Reaction equation

HRID 2298949 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:22](=[O:23])[NH:21][CH2:20][CH2:19][C:6]3=[C:7]([C:11]4[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=4)[NH:8][C:9]([CH:10]=1)=[C:5]23.C1([C:30]2[NH:31][C:32]3C=CC=C4C(=O)NCC[C:38]=2[C:37]=34)C=CC=CC=1.BrC1NC2C=C(F)C=C3C(=O)NCCC=1C=23.C(C1C=CC(B(O)O)=CC=1)=O.N1CCCC1>>[F:1][C:2]1[CH:3]=[C:4]2[C:22](=[O:23])[NH:21][CH2:20][CH2:19][C:6]3=[C:7]([C:11]4[CH:12]=[CH:13][C:14]([CH2:15][N:31]5[CH2:32][CH2:37][CH2:38][CH2:30]5)=[CH:17][CH:18]=4)[NH:8][C:9]([CH:10]=1)=[C:5]23

Participants

6

Reactant 5

HCID 31268PyrrolidineHCID 5910734-Formylphenylboronic AcidHCID 102208822-Phenyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraen-9-oneHCID 222667172-Bromo-8-fluoro-4,5-dihydro-1H-azepino[5,4,3-CD]indol-6(3H)-oneHCID 222667214-(8-Fluoro-3,4,5,6-tetrahydro-6-oxo-1H-pyrrolo(4,3,2-ef)(2)benzazepin-2-yl)benzaldehyde

Product 1

HCID 222667158-Fluoro-2-(4-pyrrolidin-1-ylmethyl-phenyl)-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one

Procedure

In a manner similar to that described for Compound PPP, 4-(8-fluoro-6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-2-yl) benzaldehyde (100 mg, 0.32 mmol; prepared in a manner similar to that described for compound 12 from 2-bromo-8-fluoro-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one and 4-formylphenylboronic acid) was reacted with pyrrolidine (115 mg, 1.62 mmol) to yield 8-fluoro-2-(4-pyrrolidin-1-ylmethyl-phenyl)-1,3,4,5-tetrahydro-azepino[5,4,3 -cd]indol-6-one, 16 mg (14%) as a yellow solid: m.p. 264-265° C. (dec), 1H NMR (300 MHz, d6-DMSO) 1.72 (m, 4H), 2.49 (m, 4H), 3.04 (m, 2H), 3.39 (m, 2H), 3.64 (br s, 2H), 7.31 (dd, J=9.3, 2.4 Hz, 1H), 7.43 (m, 3H), 7.58 (d, J=8.1 Hz, 2H), 8.2 (br t, 1H), 11.66 (br s, 1H). HRMS (MALDI MH+) Calcd for C22H22N3OF: 362.1825. Found: 364.1810. Anal. (C22H22N3OF.0.5 H2O) C, H, N.

Workup

  1. customprepared in a manner similar to

Sources & evidence

ORD record
ord-2ce5f53e0aca4737afd950d0686fcfa3
Source dataset
uspto-grants-2002_12
Patent number
US06495541B1

Reaction notes

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