HCID 6918654, compound → HCID 22640505, compound

HRID 2415122Notes

Reaction equation

HRID 2415122 reaction equation
[F:1][C:2]([F:34])([F:33])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([Cl:30])[CH:28]=4)[CH2:23][CH2:22][N:21]=3)=[CH:16][C:15]=2[O:31][CH3:32])(=[O:12])=[O:11])=[CH:6][CH:5]=1>CN(C)C=O>[F:34][C:2]([F:1])([F:33])[O:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([Cl:30])[CH:28]=4)[CH:23]=[CH:22][N:21]=3)=[CH:16][C:15]=2[O:31][CH3:32])(=[O:11])=[O:12])=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 6918654HCID 6918654, compound

Product 1

HCID 22640505HCID 22640505, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

500 mg of 1-[4-(4-Trifluoromethoxybenzenesulfonamido)-3-methoxyphenyl]-7-chloro-3,4-dihydroisoquinoline (1a) are dissolved in 500 μl of of dimethylformamide. To this solution 560 mg of potassium tert.-butylate in 4000 μl of dimethylformamide are added under an atmosphere of oxygen. The reaction mixture is stirred at RT for 4 h and evaporated to dryness. The residue is dissolved in ethyl acetate/water and the organic layer is separated. The aqueous layer is extracted twice with ethyl acetate and the combined organic layers are dried and evaporated. The product is stirred out of diethylether to yield 215 mg of the title compound.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue is dissolved in ethyl acetate/water
  3. customthe organic layer is separated
  4. extractionThe aqueous layer is extracted twice with ethyl acetate
  5. customthe combined organic layers are dried
  6. customevaporated
  7. stirringThe product is stirred out of diethylether

Sources & evidence

ORD record
ord-13d38040748e4e97ae32d5021f83f7ff
Source dataset
uspto-grants-2004_11
Patent number
US06818651B2

Reaction notes

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