4-benzyloxy-2-difluoromethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide → 2-difluoromethyl-4-hydroxy-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

HRID 1643702

반응식

HRID 1643702 반응식
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([C:10]2[CH:21]=[C:20]([O:22]CC3C=CC=CC=3)[C:13]3[CH2:14][CH:15]([CH:17]([F:19])[F:18])[O:16][C:12]=3[CH:11]=2)=[O:9])=[N:3]1>CCOC(C)=O.[Pd]>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([C:10]2[CH:21]=[C:20]([OH:22])[C:13]3[CH2:14][CH:15]([CH:17]([F:19])[F:18])[O:16][C:12]=3[CH:11]=2)=[O:9])=[N:3]1

참가 물질

4

반응물 1

HCID 595604464-benzyloxy-2-difluoromethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

생성물 1

HCID 595604162-difluoromethyl-4-hydroxy-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide수율 99.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

10% Pd on Carbon (20 mg) was added to a solution of 4-benzyloxy-2-difluoromethyl-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide (222) (186 mg, 0.466 mmol) in EtOAc (5 mL). The mixture was stirred at room temperature with a H2 balloon overnight, then filtered through Celite, washed with EtOAc, and concentrated to give yellow solid (143 mg, 99% yield). 1H NMR (400 MHz, CDCl3) δ 9.44 (br. s., 1 H) 7.27 (br. s., 1 H) 7.07 (br. s., 1 H) 6.90 (br. s., 1 H) 6.79 (br. s., 1 H) 5.67-6.04 (m, 1 H) 4.94 (br. s., 1 H) 3.73 (br. s., 3 H) 3.14-3.37 (m, 2 H); LCMS for C14H13F2N3O3 m/z 310.00 (M+H)+.

후처리

  1. filtrationfiltered through Celite
  2. washwashed with EtOAc
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e9bf5a24677f4a7c899041beec27c380
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119624B2

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