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

HRID 1741369Notes

Reaction equation

HRID 1741369 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). MS (m/z): 493 (M+ +1) IR (Nujol): 1680 cm-1NMR (CDCl3, δ): 2.15-2.45 (1H, m), 2.78-3.20 (2H, m), 2.50-2.75 (1H, m), 3.82 (3H, s), 4.38 (1H, d, J=16.2 Hz), 4.62 (1H, d, J=16.2 Hz), 5.77 (1H, t, J=7.5 Hz), 6.73 (1H, d, J=8.1 Hz), 6.76 (1H, d, J=7.5 Hz), 7.16 (1H, dd, J=7.5, 8.1 Hz), 7.32-7.34 (6H, m), 7.48-7.59 (4H, m)

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-9d63589c04ee49cebaac4c547b48e769
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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