Methyl chloroformate → HCID 49772190, compound

HRID 506114Notes

Reaction equation

HRID 506114 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:23][CH3:24])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH:20]([F:22])[F:21])[CH:11]=3)=[CH:4][CH:3]=1.Cl[C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.[Cl-].[Na+].O>[CH3:29][O:28][C:26](=[O:27])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:23][CH3:24])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH:20]([F:22])[F:21])[CH:11]=3)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 25051495HCID 25051495, compound

Product 1

HCID 49772190HCID 49772190, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 2-(4-aminophenyl)-6-difluoromethoxy-1-ethyl-1H-indole-3-carbonitrile (200 mg, 0.611 mmol) and methyl chloroformate (95 μL, 1.23 mmol) in ethyl acetate (2 mL) is treated with 2 M aqueous potassium carbonate solution (0.370 mL, 0.74 mmol), and the resulting mixture is stirred vigorously overnight. Saturated brine solution (1 mL) is added, and the mixture is stirred for 10 minutes. The organic layer is removed, dried over anhydrous magnesium sulfate, filtered and evaporated. The resulting solid is triturated with 1/1 ether-hexane, collected by filtration and dried under vacuum to afford the title product as a white solid.

Workup

  1. stirringthe mixture is stirred for 10 minutes
  2. customThe organic layer is removed
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting solid is triturated with 1/1 ether-hexane
  7. filtrationcollected by filtration
  8. customdried under vacuum

Sources & evidence

ORD record
ord-d7d20052c1da450c81335773598ea1f0
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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