(4-(chroman-6-yl)-1-(3,4-difluorobenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol → 4-(chroman-6-yl)-1-(3,4-difluorobenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

HRID 1912552ノート

反応式

HRID 1912552 の反応式
[O:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:16]([CH2:17][OH:18])=[C:15]([CH3:19])[N:14]=[C:13]4[N:20]([CH2:23][C:24]5[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=5)[CH:21]=[CH:22][C:12]=34)=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>ClCCl>[O:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[C:16]([CH:17]=[O:18])=[C:15]([CH3:19])[N:14]=[C:13]4[N:20]([CH2:23][C:24]5[CH:29]=[CH:28][C:27]([F:30])=[C:26]([F:31])[CH:25]=5)[CH:21]=[CH:22][C:12]=34)=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 71209165(4-(chroman-6-yl)-1-(3,4-difluorobenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanolHCID 178418287HCID 178418287、化合物

生成物 1

HCID 866757424-(chroman-6-yl)-1-(3,4-difluorobenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of (4-(chroman-6-yl)-1-(3,4-difluorobenzyl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol (967 mg, 2.300 mmol) in dichloromethane (DCM) (24 mL) was treated with PCC (644 mg, 2.99 mmol) and the mixture was stirred at ambient temperature for 90 minutes. The mixture was diluted with dichloromethane, filtered over Celite™ and the filtrate was concentrated. The residue was purified on silica gel (0-70% ethyl acetate/hexanes) to afford the desired product as a pale yellow foam: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 10.11 (s, 1 H), 7.22 (dd, J=2.1, 8.4 Hz, 1 H), 7.16-7.04 (m, 4 H), 7.04-6.97 (m, 1 H), 6.93 (d, J=8.4 Hz, 1 H), 6.44 (d, J=3.5 Hz, 1 H), 5.47 (s, 2 H), 4.37-4.20 (m, 2 H), 2.95 (s, 3 H), 2.86 (t, J=6.4 Hz, 2 H), 2.20-1.96 (m, 2 H); LC/MS (m/z) ES+=419 (M+1).

後処理

  1. filtrationfiltered over Celite™
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified on silica gel (0-70% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-604e89c35b4f49748ebda284243de9c0
出典データセット
uspto-grants-2013_12
特許番号
US08609653B2

反応ノート

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