Stannous chloride dihydrate → Dimethylcarbamic acid 3-(3-amino-2-fluorobenzyl)-4-fluoromethyl-2-oxo-2H-1-benzopyran-7-yl ester

HRID 1046786Notes

Reaction equation

HRID 1046786 reaction equation
[F:1][CH2:2][C:3]1[C:8]2[CH:9]=[CH:10][C:11]([O:13][C:14](=[O:18])[N:15]([CH3:17])[CH3:16])=[CH:12][C:7]=2[O:6][C:5](=[O:19])[C:4]=1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-])=O)[C:22]=1[F:30].O.O.[Sn](Cl)Cl.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[NH2:27][C:23]1[C:22]([F:30])=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][C:4]1[C:5](=[O:19])[O:6][C:7]2[CH:12]=[C:11]([O:13][C:14](=[O:18])[N:15]([CH3:17])[CH3:16])[CH:10]=[CH:9][C:8]=2[C:3]=1[CH2:2][F:1]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 59139149HCID 59139149, compound

Product 1

HCID 59139194Dimethylcarbamic acid 3-(3-amino-2-fluorobenzyl)-4-fluoromethyl-2-oxo-2H-1-benzopyran-7-yl esterYield 102.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl acetate (2.0 mL) was added to dimethylcarbamic acid 4-fluoromethyl-3-(2-fluoro-3-nitrobenzyl)-2-oxo-2H-1-benzopyran-7-yl ester (20.5 mg) (6c-1-4), and tin(II) chloride dihydrate (60 mg) was added to the resultant suspension while stirring at room temperature. The suspension was heated under reflux for 1.5 hours, and after cooling to room temperature, saturated sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. The resultant organic layer extraction liquid was washed with saturated saline, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was then distilled away under reduced pressure to yield the title compound (19.5 mg).

Workup

  1. temperatureThe suspension was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureafter cooling to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. extractionThe resultant organic layer extraction liquid
  6. washwas washed with saturated saline
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. distillationThe solvent was then distilled away under reduced pressure

Sources & evidence

ORD record
ord-5aa153d08a044fb09b87cca4b1d0ea92
Source dataset
uspto-grants-2013_10
Patent number
US08569378B2

Reaction notes

Loading…