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

HRID 2213683Notes

Reaction equation

HRID 2213683 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21992828Pyridine ethyl acetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-743a2c106754474cb93ef5721c424bdd
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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