Dimethylformamide → HCID 118667044, compound

HRID 591515Notes

Reaction equation

HRID 591515 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[C:18](Cl)=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=3)=[CH:14][C:9]=2[S:8][CH:7]=1)[CH3:2].[NH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>O>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[C:18]([N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=3)=[CH:14][C:9]=2[S:8][CH:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 118667043HCID 118667043, compound

Product 1

HCID 118667044HCID 118667044, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of ethyl(6-((2-chloro-6-(trifluoromethyl)pyridin-3-yl)methoxy)-1-benzothiophen-3-yl)acetate (90 mg), pyrrolidine (59.6 mg) and DMF (dry) (10 mL) was added K2CO3 (57.9 mg). The mixture was stirred at 80° C. under argon atmosphere overnight. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give title compound (46.0 mg).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-836fe3e2af284486b1e7b8444c7228c9
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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