Ethyl Acetate → HCID 86654955, compound

HRID 1615605Notes

Reaction equation

HRID 1615605 reaction equation
[C:1]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([C:16]=1[N:17]1[C:22](=[O:23])[C:21]3=[CH:24][S:25][CH:26]=[C:20]3[N:19]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:18]1=[O:34])=[CH:14][C:13]([C:35]([F:38])([F:37])[F:36])=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[F:45][C:46]1[CH:53]=[CH:52][C:51]([F:54])=[CH:50][C:47]=1[CH2:48]Br.C(OCC)(=O)C>C1COCC1.CN(C=O)C>[C:1]([O:5][C:6]([C:8]1[N:9]([CH2:48][C:47]2[CH:50]=[C:51]([F:54])[CH:52]=[CH:53][C:46]=2[F:45])[C:10]2[C:15]([C:16]=1[N:17]1[C:22](=[O:23])[C:21]3=[CH:24][S:25][CH:26]=[C:20]3[N:19]([C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[C:18]1=[O:34])=[CH:14][C:13]([C:35]([F:36])([F:37])[F:38])=[CH:12][CH:11]=2)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 5228302-(Bromomethyl)-1,4-difluorobenzeneHCID 23665647Potassium tert-butoxideHCID 86654954HCID 86654954, compound

Product 1

HCID 86654955HCID 86654955, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-tert-butoxycarbonyl-2,4-dioxo-1,2-dihydro-4H-thieno[3,4-d]pyrimidin-3-yl)-5-trifluoromethyl-1H-indole-2-carboxylic acid tert-butyl ester 51 (30 mg, 0.054 mmol) in anhydrous THF (1 mL) and anhydrous DMF (1 mL) was added potassium tert-butoxide (9 mg, 0.080 mmol) and 2,5-difluorobenzyl bromide 5J (14.6 mg, 0.071 mmol). The reaction mixture was stirred at room temperature for 3 hours. Ethyl acetate (50 mL) was added and the organic layer was washed with saturated ammonium chloride solution and brine. The organic layer was dried over sodium sulfate. The organic solvent was removed under reduced pressure to provide 3-(1-tert-butoxycarbonyl-2,4-dioxo-1,2-dihydro-4H-thieno[3,4-d]pyrimidin-3-yl)-1-(2,5-difluorobenzyl)-5-trifluoromethyl-1H-indole-2-carboxylic acid tert-butyl ester 5K which was used in the next step without further purification.

Workup

  1. washthe organic layer was washed with saturated ammonium chloride solution and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customThe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2f466ffb76fc4611a2e0863579defdd4
Source dataset
uspto-grants-2014_07
Patent number
US08765757B2

Reaction notes

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