Boron tribromide → HCID 59426398, compound

HRID 252533Notes

Reaction equation

HRID 252533 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, is stirred in BBr3 (800 μL, 1M in CH2Cl2, 0.8 mmol) at room temperature for 1 hour. The reaction mixture is quenched with H2O, and is extracted with CH2Cl2. The organic layer is dried and concentrated. Purification by silica chromatography (EtOAC) gives impure product. This crude product is 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 is quenched with H2O
  2. extractionis extracted with CH2Cl2
  3. customThe organic layer is dried
  4. concentrationconcentrated
  5. customPurification by silica chromatography (EtOAC)
  6. customgives impure product
  7. customThis crude product is triturated with 1/1 hexanes/acetone

Sources & evidence

ORD record
ord-fd0cefbbb9c44921bc68f1dad56124a7
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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