trans-4-amino-3,4-dihydro-2,2-dimethyl-6-trifluoromethylsulfonyl 2H-1-benzopyran-3-ol → trans-4-(4-Fluoro-1-oxoisoindolin-2-yl)-3,4-dihydro-2,2-dimethyl-6-trifluoromethylsulfonyl-2H-1-benzopyran-3-ol

HRID 1656461Notes

Reaction equation

HRID 1656461 reaction equation
Br[CH2:2][C:3]1[C:12]([F:13])=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=O.[NH2:14][C@@H:15]1[C:20]2[CH:21]=[C:22]([S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])[CH:23]=[CH:24][C:19]=2[O:18][C:17]([CH3:33])([CH3:32])[C@H:16]1[OH:34]>C(N(CC)CC)C>[F:13][C:12]1[CH:11]=[CH:10][CH:9]=[C:4]2[C:3]=1[CH2:2][N:14]([C@@H:15]1[C:20]3[CH:21]=[C:22]([S:25]([C:28]([F:30])([F:31])[F:29])(=[O:27])=[O:26])[CH:23]=[CH:24][C:19]=3[O:18][C:17]([CH3:32])([CH3:33])[C@H:16]1[OH:34])[C:5]2=[O:7]

Participants

4

Reactant 2

HCID 15036014trans-4-amino-3,4-dihydro-2,2-dimethyl-6-trifluoromethylsulfonyl 2H-1-benzopyran-3-olHCID 19788116Methyl 2-(bromomethyl)-3-fluorobenzoate

Product 1

HCID 67858882trans-4-(4-Fluoro-1-oxoisoindolin-2-yl)-3,4-dihydro-2,2-dimethyl-6-trifluoromethylsulfonyl-2H-1-benzopyran-3-olYield 63.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following the procedure and working up described in Example 12, but using 0.272 g of methyl 2-bromomethyl-3-fluorobenzoate, 0.326 g of trans-4-amino-3,4-dihydro-2,2-dimethyl 6-trifluoromethylsulfonyl-2H-1-benzopyran- 3-ol and 0.15 ml of triethylamine, 0.294 g of the title compound, melting at 259°-261° C., was obtained after purification by column chromatography through silica gel, using a 1:1 by volume mixture of cyclohexane and ethyl acetate as the eluent, followed by recrystallization from a mixture of ethyl acetate and hexane.

Sources & evidence

ORD record
ord-e004dd9475ed42d793679504ad291902
Source dataset
uspto-grants-1993_10
Patent number
US05254578

Reaction notes

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