Potassium Carbonate → 1-(N-trifluoroacetyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene

HRID 380103Notes

Reaction equation

HRID 380103 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([NH:5][CH:6]1[C:14]2[C:9](=[C:10]([O:15][CH3:16])[CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)=[O:4].[C:19]1([C:25]2[N:26]=[C:27]([CH2:36]Br)[O:28][C:29]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:1][C:2]([F:17])([F:18])[C:3]([N:5]([CH:6]1[C:14]2[C:9](=[C:10]([O:15][CH3:16])[CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)[CH2:36][C:27]1[O:28][C:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:26]=1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5685992-Bromomethyl-4,5-diphenyl-oxazoleHCID 183673621-trifluoroacetamido-2,3-dihydro-4-methoxy-1H-indene

Product 1

HCID 183673231-(N-trifluoroacetyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indeneYield 35.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-trifluoroacetamido-2,3-dihydro-4-methoxy-1H-indene (0.44 g) and 4,5-diphenyl-2-bromomethyloxazole (0.55 g) in DMF was added K2CO3 (0.30 g). After being stirred for 12 hours, the solution was extracted with ethyl acetate. The mixture was washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 1-(N-trifluoroacetyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene (0.30 g).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe mixture was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c6d572ae84444f02a89ff56483674ed1
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Reaction notes

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