Phosphorus tribromide → HCID 86660456, compound

HRID 2039965Notes

Reaction equation

HRID 2039965 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[CH:15]=[C:14]([CH2:16]O)[NH:13][C:10]2=[N:11][CH:12]=1)=[O:5].P(Br)(Br)[Br:23]>O1CCCC1>[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[CH:15]=[C:14]([CH2:16][Br:23])[NH:13][C:10]2=[N:11][CH:12]=1)=[O:5]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 49766392HCID 49766392, compound

Product 1

HCID 86660456HCID 86660456, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A flask is charged successively with 1 g (2.89 mmol) of 2-bromo-N-(2-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide (Example 16), 100 mL of tetrahydrofuran and 408 μL (4.34 mmol) of phosphorus bromide (PBr3) under argon atmosphere. It is stirred at room temperature for 18 hours. The solvent is then evaporated under reduced pressure, and the residue is taken up in 150 mL of ethyl acetate. The organic phase is washed with 3×50 mL of water, dried over sodium sulphate and evaporated under reduced pressure. The precipitate obtained is dried under vacuum for 1 h, finally obtaining 957 mg of a brown solid (raw yield 81%).

Workup

  1. customThe solvent is then evaporated under reduced pressure
  2. washThe organic phase is washed with 3×50 mL of water
  3. dry with materialdried over sodium sulphate
  4. customevaporated under reduced pressure
  5. customThe precipitate obtained
  6. customis dried under vacuum for 1 h

Sources & evidence

ORD record
ord-9c4eb020c91d4bd2b1dab8fce4a0c36b
Source dataset
uspto-grants-2013_11
Patent number
US08580815B2

Reaction notes

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