Acetic Acid → HCID 23152807, compound

HRID 1012234Notes

Reaction equation

HRID 1012234 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[NH:10][C:11]2[C:16]([C:17]=1[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[CH:15][CH:14]=[C:13]([C:24]([O:26][CH3:27])=[O:25])[CH:12]=2.C([O-])(=O)C.[Na+].C(O)(=O)C.[Cl:37][CH2:38][C:39](Cl)=[O:40].C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:37][CH2:38][C:39]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[NH:10][C:11]2[C:16]([C:17]=1[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[CH:15][CH:14]=[C:13]([C:24]([O:26][CH3:27])=[O:25])[CH:12]=2)=[O:40]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 23152898HCID 23152898, compound

Product 1

HCID 23152807HCID 23152807, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyl 2-(2-amino-5-fluorophenyl)-3-cyclohexyl-1H-indole-6-carboxylate (2.44 g, 6.68 mmol), sodium acetate (602 mg, 7.3 mmol) and acetic acid (0.45 ml, 7.86 mmol) in tetrahydrofuran (20 ml) was added dropwise chloroacetyl chloride (0.60 ml, 7.53 mmol), and the mixture was stirred at room temperature for 2 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium carbonate solution and saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and a mixed solvent of hexane:ethyl acetate (4:1) was added to the residue. The precipitated solid was collected by filtration to give methyl 2-[2-(2-chloroacetylamino)-5-fluorophenyl]-3-cyclohexyl-1H-indole-6-carboxylate (2.5 g, yield 84.7%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with saturated aqueous sodium carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. additiona mixed solvent of hexane:ethyl acetate (4:1) was added to the residue
  7. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-b1ae5eac970644618b1ab14c3b6e977b
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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