HCID 10252039, 화합물 → 3-(2-methoxy-4-methoxycarbonyl-benzyl)-1H-indole-5-carboxylic acid

HRID 1739590노트

반응식

HRID 1739590 반응식
[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22]CC4C=CC=CC=4)=[O:21])[CH:18]=3)[NH:13][CH:12]=2)=[C:6]([O:30][CH3:31])[CH:5]=1>CN(C)C=O.C(O)=O.[Pd]>[CH3:31][O:30][C:6]1[CH:5]=[C:4]([C:3]([O:2][CH3:1])=[O:32])[CH:9]=[CH:8][C:7]=1[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([OH:22])=[O:21])[CH:18]=2)[NH:13][CH:12]=1

참가 물질

5

반응물 1

HCID 10252039HCID 10252039, 화합물

생성물 1

HCID 103372503-(2-methoxy-4-methoxycarbonyl-benzyl)-1H-indole-5-carboxylic acid수율 73%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 284Formic Acid용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-[5-benzoxycarbonyl-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid methylester (3.46 grams, 8.06 mmol) in dimethylformamide (40 mL) and formic acid (2 mL) was added 10% palladium on carbon (1.5 grams). The resulting mixture was hydrogenated at 30 psi for 1.5 hours. The mixture was filtered through celite and the filtrate diluted with ethyl acetate. This solution was washed several times with 1 M hydrochloric acid (aq). The organics were then dried over magnesium sulfate and concentrated. Recrystallization from methylene chloride gave 3-(2-methoxy-4-methoxycarbonyl-benzyl)-1H-indole-5-carboxylic acid (1.97 grams, 73% yield).

후처리

  1. filtrationThe mixture was filtered through celite
  2. additionthe filtrate diluted with ethyl acetate
  3. washThis solution was washed several times with 1 M hydrochloric acid (aq)
  4. dry with materialThe organics were then dried over magnesium sulfate
  5. concentrationconcentrated
  6. customRecrystallization from methylene chloride

출처 및 근거

ORD 기록
ord-64322bc4749042dda6e38d1988468d9d
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05965745

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