Potassium Carbonate → methyl 4-methyl-3-[1-oxo-7-{[(trifluoromethyl)sulfonyl]oxy} isoquinolin-2(1H)-yl]benzoate

HRID 506981Notes

Reaction equation

HRID 506981 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=3[CH3:23])[C:16]([O:18][CH3:19])=[O:17])[C:9]2=[O:12])=[CH:4][CH:3]=1.C1(N[S:31]([C:34]([F:37])([F:36])[F:35])(=[O:33])=[O:32])C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH3:23][C:22]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]=1[N:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][C:2]([O:1][S:31]([C:34]([F:37])([F:36])[F:35])(=[O:33])=[O:32])=[CH:3][CH:4]=2)[C:9]1=[O:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 67018571methyl 3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzoate

Product 1

HCID 86620854methyl 4-methyl-3-[1-oxo-7-{[(trifluoromethyl)sulfonyl]oxy} isoquinolin-2(1H)-yl]benzoateYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

Methyl 3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzoate (529 mg), N-phenyltrifluoromethanesulfonamide (612 mg) and potassium carbonate (709 mg) were stirred in THF (15 ml) and heated under microwave irradiation (Personal Chemistry Emrys Optimizer with 300 W magnetron) at 120° C. for 10 minutes. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate and washed with water (×2), brine, dried (magnesium sulfate) and concentrated. Purification by column chromatography with a gradient of iso-hexane to 30% ethyl acetate/iso-hexane yielded methyl 4-methyl-3-[1-oxo-7-{[(trifluoromethyl)sulfonyl]oxy} isoquinolin-2(1H)-yl]benzoate as a white solid (613 mg); NMR Spectrum: (DMSOd6) 2.15 (s, 3H), 3.86 (s, 3H), 6.89 (d, 1H), 7.50 (d, 1H), 7.60 (d, 1H), 7.90 (s, 1H), 7.93 (d, 1H), 8.00 (m, 2H), 8.20 (s, 1H); Mass Spectrum: M+Na+ 464.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water (×2), brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. customPurification by column chromatography with a gradient of iso-hexane to 30% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-a26e388aa6184b8387553dba41f26b9d
Source dataset
uspto-grants-2010_08
Patent number
US07786115B2

Reaction notes

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