Pyrrolidine → Indol-6-one

HRID 33345

反応式

HRID 33345 の反応式
F[C:2]1[CH:3]=[C:4]2C(=O)NCC[C:6]3=[C:7](C4C=CC(C=O)=CC=4)[NH:8][C:9]([CH:10]=1)=[C:5]23.C1(C2NC3C=CC=C4C(=[O:43])NCCC=2C=34)C=CC=CC=1.BrC1N(F)C2C=C(F)C=C3C(=O)NCCC=1C=23.C(C1C=CC(B(O)O)=CC=1)=O.N1CCCC1>>[N:8]1[C:9]2[C:5]([CH:4]=[CH:3][C:2](=[O:43])[CH:10]=2)=[CH:6][CH:7]=1

参加物

6

反応物 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 222667214-(8-Fluoro-3,4,5,6-tetrahydro-6-oxo-1H-pyrrolo(4,3,2-ef)(2)benzazepin-2-yl)benzaldehydeHCID 692767222-Bromo-8-fluoro-fluoro-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one

生成物 1

HCID 17925780Indol-6-one

実験手順

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-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-azepinop5,4,3-cd]indol-6-one, 16 mg (14%) as a yellow solid: m.p. 264-265° C. (dec), 1H NMR (300 MHz, d6-DMSO) δ 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), 8.25 (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.

後処理

  1. customprepared in a manner similar to

出典と根拠

ORDレコード
ord-b56498e2b2fc4286a0b0e54e2b447550
出典データセット
uspto-grants-2008_09
特許番号
US07429578B2

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