Potassium Carbonate → HCID 70663174, compound

HRID 878310Notes

Reaction equation

HRID 878310 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N:14]([CH3:31])[C:15](=[O:30])[C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:17]=1.C([O-])([O-])=O.[K+].[K+].I[CH:39]1[CH2:42][O:41][CH2:40]1.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:29][S:26]([C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([C:22]([F:24])([F:25])[F:23])[CH:19]=1)[C:15]([N:14]([CH3:31])[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH:39]1[CH2:42][O:41][CH2:40]1)=[O:30])(=[O:28])=[O:27]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 133566863-IodooxetaneHCID 136414058HCID 136414058, compound

Product 1

HCID 70663174HCID 70663174, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution N-(4-(2-hydroxyphenyl)pyridin-3-yl)-N-methyl-3-(methylsulfonyl)-5-(trifluoromethyl)benzamide (100 mg, 222 μmol, example 263, intermediate a) in DMF (2 ml) was added K2CO3 (61.4 mg, 444 μmol) and 3-iodooxetane (44.9 mg, 244 μmol). The reaction mixture was stirred for 18 hours at 80° C. The reaction mixture was poured on 30 mL 10% aqueous NaHCO3 solution and 30 mL EtOAc and the layers were separated. The aqueous layer was extracted a second time with 30 mL EtOAc. The organic layers were washed with 30 mL brine, dried over MgSO4, filtered and concentrated under vacuum. The compound was purified by silica gel chromatography on a 20 g column using an MPLC (Flashmaster) system eluting with a gradient of n-heptane:EtOAc (100:0 to 0:100). Colorless foam (52 mg, 46%). MS (ESI): m/z=507.120 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted a second time with 30 mL EtOAc
  3. washThe organic layers were washed with 30 mL brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe compound was purified by silica gel chromatography on a 20 g column
  8. washeluting with a gradient of n-heptane:EtOAc (100:0 to 0:100)

Sources & evidence

ORD record
ord-071547ef6d404c22958c421b411a5cc5
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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