2-(benzyloxy)-N-(5-(1-methyl-1H-indol-2-yl)pyridin-3-yl)ethanesulfonamide → 2-hydroxy-N-(5-(1-methyl-1H-indol-2-yl)pyridin-3-yl)ethanesulfonamide

HRID 1661735ノート

反応式

HRID 1661735 の反応式
C([O:8][CH2:9][CH2:10][S:11]([NH:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]2[N:22]([CH3:30])[C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=1)(=[O:13])=[O:12])C1C=CC=CC=1>[Pd].CO>[OH:8][CH2:9][CH2:10][S:11]([NH:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]2[N:22]([CH3:30])[C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=1)(=[O:13])=[O:12]

参加物

4

反応物 1

HCID 595346672-(benzyloxy)-N-(5-(1-methyl-1H-indol-2-yl)pyridin-3-yl)ethanesulfonamide

生成物 1

HCID 595346512-hydroxy-N-(5-(1-methyl-1H-indol-2-yl)pyridin-3-yl)ethanesulfonamide

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

A flask is charged with 2-(benzyloxy)-N-(5-(1-methyl-1H-indol-2-yl)pyridin-3-yl)ethanesulfonamide (90 mg, 0.214 mmol) and MeOH (5 mL), and the flask is flushed with N2. 10% Pd/C (22.7 mg, 0.021 mmol) is added to the mixture. The flask is flushed with H2 and stirred under H2 atmosphere at 50° C. overnight. The mixture is filtered and the filtrate is purified by silica chromatography eluting with a 0 to 4% methanol-DCM gradient to give 2-hydroxy-N-(5-(1-methyl-1H-indol-2-yl)pyridin-3-yl)ethanesulfonamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.37 (t, J=6.2 Hz, 2H), 3.77 (s, 3H), 3.80 (t, J=6.3 Hz, 2H), 4.96 (br. s., 1H), 6.70 (s, 1H), 7.10 (t, J=7.1 Hz, 1H), 7.23 (td, J=7.6, 1.1 Hz, 1H), 7.53 (d, J=7.8 Hz, 1H), 7.61 (d, J=7.8 Hz, 1H), 7.79 (t, J=2.3 Hz, 1H), 8.47 (d, J=2.5 Hz, 1H), 8.55 (d, J=1.8 Hz, 1H), 10.12 (br. s., 1H). HRMS: (ESI) m/z 332.1072 [(M+H)+ Calcd for C16H18N3O3S 332.1063].

後処理

  1. customthe flask is flushed with N2
  2. customThe flask is flushed with H2
  3. filtrationThe mixture is filtered
  4. customthe filtrate is purified by silica chromatography
  5. washeluting with a 0 to 4% methanol-DCM gradient

出典と根拠

ORDレコード
ord-938fef0599c54ace82f53216634242f8
出典データセット
uspto-grants-2011_10
特許番号
US08030334B2

反応ノート

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