hydroxylamine-O-sulfonic acid → 1-Amino-3-(4-fluorophenyl)-5-methyl-1H-indole

HRID 275363

반응식

HRID 275363 반응식
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([CH3:23])[CH:21]=3)[NH:16][CH:15]=2)=[CH:10][CH:9]=1.[NH2:24]OS([O-])(=O)=O.[K+].NOS(O)(=O)=O>CN(C=O)C>[NH2:24][N:16]1[C:17]2[C:22](=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[C:14]([C:11]2[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=2)=[CH:15]1

참가 물질

6

반응물 4

HCID 76284hydroxylamine-O-sulfonic acidHCID 103763663-(4-fluorophenyl)-5-methyl-1H-indoleHCID 23665647Potassium tert-butoxide2회HCID 23710068potassium hydroxylamine-O-sulphonate

생성물 1

HCID 100830041-Amino-3-(4-fluorophenyl)-5-methyl-1H-indole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

Potassium tert-butoxid (7.5 g) was added to a solution of 3-(4-fluorophenyl)-5-methyl-1H-indole 1c (15 g) in DMF during 15 min at 0°-5° C. Then a suspension of potassium hydroxylamine-O-sulphonate in DMF (prepared by addition of potassium tert-butoxid (7.5 g) to a suspension of hydroxylamine-O-sulphonic acid (7.6 g) in DMF (100 ml) during 0.5 h at 0°-5° C.) was added slowly at 0°-5° C. After reaction at 0° C. for 1 h the mixture was poured into ice, and extracted with diethyl ether (2×250 ml). The combined organic phases were washed with brine (3×250 ml) and dried (Na2SO4). Evaporation of the solvents afforded the title compound which was purified by column chromatography on silica gel (eluted with ethyl acetate/heptane 1:3) and crystallized from diethylether. Yield: 4.3 g, mp 116°-120° C.

후처리

  1. additionwas added slowly at 0°-5° C
  2. customAfter reaction at 0° C. for 1 h the mixture
  3. additionwas poured into ice
  4. extractionextracted with diethyl ether (2×250 ml)
  5. washThe combined organic phases were washed with brine (3×250 ml)
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvents

출처 및 근거

ORD 기록
ord-ea17ac9be48d428a88c8b5c89c9d4ea2
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05393761

연결된 노트

불러오는 중…