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 1661735노트

반응식

HRID 1661735 반응식
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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

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온도
50 °C

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-938fef0599c54ace82f53216634242f8
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030334B2

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