Oxalyl chloride → HCID 66680686, compound

HRID 1626740Notes

Reaction equation

HRID 1626740 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:17])[C:12]([C:18]([OH:20])=O)=[CH:11]2.[NH2:21][C:22]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25].O.C(=O)(O)[O-].[Na+]>CC(N(C)C)=O.C1COCC1.CN(C=O)C>[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH3:17])[C:12]([C:18]([NH:21][C:22]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:23]=1[C:24]([O:26][CH3:27])=[O:25])=[O:20])=[CH:11]2

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 78878Methyl 2-amino-5-chlorobenzoateHCID 620146HCID 620146, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 66680686HCID 66680686, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 31374DimethylacetamideSolvent

Procedure

A catalytic amount of DMF and 560 mg (4.41 mmol) of oxalyl chloride were added to a THF (8 mL) solution comprising 800 mg (3.15 mmol) of 5-bromo-1-methyl-1H-indole-2-carboxylic acid at 0° C., and the mixture was stirred at room temperature for 40 minutes. After the solvent was distilled off under reduced pressure, 8 mL of DMAc and 585 mg (3.15 mmol) of methyl 2-amino-5-chlorobenzoate were added to the residue in this order at 0° C., and the mixture was stirred at room temperature for 1 hour. After the completion of the reaction, saturated sodium bicarbonate water was added under ice-cooling, and the mixture was stirred. The resulting solids were collected by filtration, washed with water, and dried under reduced pressure at 50° C. for 3 hours, thereby giving 1.22 g of methyl 2-{[(5-bromo-1-methyl-1H-indol-2-yl)carbonyl]amino}-5-chlorobenzoate (yield: 92%).

Workup

  1. additionwere added to the residue in this order at 0° C.
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. additionwas added under ice-
  4. temperaturecooling
  5. stirringthe mixture was stirred
  6. filtrationThe resulting solids were collected by filtration
  7. washwashed with water
  8. customdried under reduced pressure at 50° C. for 3 hours

Sources & evidence

ORD record
ord-74ee75eb83284ee79d801fb6d7edb21d
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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