Dichloromethane → HCID 118071484, compound

HRID 2207728Notes

Reaction equation

HRID 2207728 reaction equation
[F:1][CH:2]([F:23])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17]C)[CH:15]=2)[NH:10][C:9]=1[C:19]([NH:21][CH3:22])=[O:20])=[O:4].ClCCl.B(Br)(Br)Br>CO>[F:23][CH:2]([F:1])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[NH:10][C:9]=1[C:19]([NH:21][CH3:22])=[O:20])=[O:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 72948196HCID 72948196, compound

Product 1

HCID 118071484HCID 118071484, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 3-{2-[(difluoroacetyl)amino]ethyl}-5-methoxy-N-methyl-1H-indole-2-carboxamide (2.52 g) and dichloromethane (50.0 mL) was added boron tribromide (1.0 M dichloromethane solution, 23.3 mL) under ice-cooling, followed by slowly warming to room temperature, and then stirring at room temperature overnight. The reaction mixture was cooled to −15° C. and methanol (5.00 mL) was added thereto, followed by warming to room temperature. The reaction mixture was concentrated under reduced pressure and then the residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 5:1) to obtain 3-{2-[(difluoroacetyl)amino]ethyl}-5-hydroxy-N-methyl-1H-indole-2-carboxamide (2.37 g) as a yellow solid.

Workup

  1. temperaturecooling
  2. temperatureThe reaction mixture was cooled to −15° C.
  3. temperatureby warming to room temperature
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 5:1)

Sources & evidence

ORD record
ord-fd0a2117b332441386c61664c2005879
Source dataset
uspto-grants-2016_06
Patent number
US09376449B2

Reaction notes

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