Dichloromethane → HCID 118071484, compound

HRID 1775432Notes

Reaction equation

HRID 1775432 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-0a6d9e7e2d8d4bd4a62d1275a30265b4
Source dataset
uspto-grants-2016_02
Patent number
US09260445B2

Reaction notes

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