1,1,1-Trifluoro-N-phenylmethanesulfonamide → HCID 87158322, compound

HRID 1844073Notes

Reaction equation

HRID 1844073 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:18]=3[CH:19]3[CH2:21][CH2:20]3)[C:9]2=[O:12])=[CH:4][C:3]=1[OH:22].C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(N[S:40]([C:43]([F:46])([F:45])[F:44])(=[O:42])=[O:41])C=CC=CC=1>C1COCC1>[F:44][C:43]([F:46])([F:45])[S:40]([O:22][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[Cl:1])[C:9](=[O:12])[N:8]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[CH:19]1[CH2:20][CH2:21]1)[CH2:7][CH2:6]2)(=[O:42])=[O:41]

Participants

5

Reactant 3

HCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 89964493HCID 89964493, compound

Product 1

HCID 87158322HCID 87158322, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-Chloro-6-hydroxy-2-(4-cyclopropylpyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one (90A: 180 mg, 0.57 mmol) was reacted with KHMDS (0.71 mL, 0.71 mmol) in THF (10 mL) and N-phenyl trifluoromethanesulfonamide (226 mg, 0.630 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% methanol in CHCl3) afforded 170 mg of the product (66.6% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1% methanol in CHCl3)

Sources & evidence

ORD record
ord-2d66d1d03ee24a6790627e14e75882ae
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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