Boron tribromide → HCID 59426398, compound

HRID 907140Notes

Reaction equation

HRID 907140 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12]C)=[CH:9][CH:10]=2)[N:5]([CH2:14][CH3:15])[C:4]=1[C:16]#[C:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([CH:27]2[CH2:29][CH2:28]2)=[O:26])=[CH:20][CH:19]=1)#[N:2].B(Br)(Br)Br>>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[N:5]([CH2:14][CH3:15])[C:4]=1[C:16]#[C:17][C:18]1[CH:19]=[CH:20][C:21]([NH:24][C:25]([CH:27]2[CH2:28][CH2:29]2)=[O:26])=[CH:22][CH:23]=1)#[N:2]

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 59425988HCID 59425988, compound

Product 1

HCID 59426398HCID 59426398, compoundYield 54.1%

Procedure

Cyclopropanecarboxylic acid [4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-ylethynyl)-phenyl]-amide (60 mg, 0.16 mmol), prepared as described in example 1Za, was stirred in BBr3 (800 μL, 1M in CH2Cl2, 0.8 mmol) at room temperature for 1 hour. The reaction mixture was quenched with H2O, and was extracted with CH2Cl2. The organic layer was dried and concentrated. Purification by silica chromatography (EtOAC) gave impure product. These crude product was triturated with 1/1 hexanes/acetone to yield cyclopropanecarboxylic acid [4-(3-cyano-1-ethyl-6-hydroxy-1H-indol-2-ylethynyl)-phenyl]-amide (32 mg, 54%) as an off-white solid.

Workup

  1. customThe reaction mixture was quenched with H2O
  2. extractionwas extracted with CH2Cl2
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customPurification by silica chromatography (EtOAC)
  6. customgave impure product
  7. customThese crude product was triturated with 1/1 hexanes/acetone

Sources & evidence

ORD record
ord-f5e062d5d605408c96adee601fd00727
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

Loading…