Stannous chloride dihydrate → 5-Amino-3-[(4-(dimethylethoxycarbonylaminomethyl)pyrrol-2-yl)methylene]indolin-2-one

HRID 2213683노트

반응식

HRID 2213683 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=[CH:14][C:15]1[NH:16][CH:17]=[C:18]([C:20]([CH3:28])([CH3:27])[NH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:19]=1)([O-])=O.O.O.[Sn](Cl)Cl>C(OCC)(=O)C.N1C=CC=CC=1>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=[CH:14][C:15]1[NH:16][CH:17]=[C:18]([C:20]([CH3:27])([CH3:28])[NH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:19]=1

참가 물질

4

반응물 2

HCID 61436Stannous chloride dihydrateHCID 695891135-Nitro-3-[(4-(dimethylethoxycarbonylaminomethyl)-pyrrol-2-yl)methylene]indolin-2-one

생성물 1

HCID 695895105-Amino-3-[(4-(dimethylethoxycarbonylaminomethyl)pyrrol-2-yl)methylene]indolin-2-one수율 95.9%

시약·촉매·용매 1

HCID 21992828Pyridine ethyl acetate용매

실험 절차

To a suspension of 5-nitro-3-[(4-(dimethylethoxycarbonylaminomethyl)-pyrrol-2-yl)methylene]indolin-2-one (0.8 g, 2 mmol) in ethyl acetate/pyridine (60 mL/9 mL) was added tin (II) chloride dihydrate and the reaction mixture was refluxed for 1.5 hours. The reaction mixture was cooled to ambient temperature, filtered through celite and the filtrate was partitioned in water and ethyl acetate. The organic layer was washed with water and filtered again through celite. The organic layer was then washed with brine, and concentrated to afford 5-amino-3-[(4-(dimethylethoxycarbonylaminomethyl)pyrrol-2-yl)methylene]indolin-2-one as a red colored solid (0.68 g); 1H NMR (400 MHz, DMSO) δ 1.38 (s, 9H), 2.62 (s, 3H), 4.0 (d, 2H), 4.64 (s, 2H), 6.42 (d, 1H), 6.58 (d, 1H), 6.82 (s, 1H), 7.0 (s, 1H), 8.08 (m, 2H), 10.52 (s, 1H) ppm. Hydrolysis under standard conditions yielded 5-amino-3-[(4-(aminomethyl)pyrrol-2-yl)methylene]indolin-2-one; 1H NMR (400 MHz, DMSO-d6) δ 2.66 (s, 3H), 4.00 (m, 2H), 6.50. (dd, 1H), 6.64 (d, 1H), 7.08 (s, 1H), 7.26 (s, 1H), 7.38 (s, 1H), 8.06 (brs, 1H), 10.18 (s, 1H) ppm.

후처리

  1. temperaturethe reaction mixture was refluxed for 1.5 hours
  2. filtrationfiltered through celite
  3. customthe filtrate was partitioned in water
  4. washThe organic layer was washed with water
  5. filtrationfiltered again through celite
  6. washThe organic layer was then washed with brine
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-743a2c106754474cb93ef5721c424bdd
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07105563B2

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