Phosphorus tribromide → HCID 86720652, compound

HRID 875453Notes

Reaction equation

HRID 875453 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([CH2:25]O)[CH:22]=[C:21]([Cl:27])[C:3]=1[C:4]([C:6]1[C:14]2[C:9](=[C:10]([NH:15][C:16]([CH:18]3[CH2:20][CH2:19]3)=[O:17])[N:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)=[O:5].P(Br)(Br)[Br:29]>ClCCl.C(Cl)(Cl)(Cl)Cl>[Br:29][CH2:25][C:23]1[CH:24]=[C:2]([Cl:1])[C:3]([C:4]([C:6]2[C:14]3[C:9](=[C:10]([NH:15][C:16]([CH:18]4[CH2:20][CH2:19]4)=[O:17])[N:11]=[CH:12][CH:13]=3)[NH:8][CH:7]=2)=[O:5])=[C:21]([Cl:27])[CH:22]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 71061313HCID 71061313, compound

Product 1

HCID 86720652HCID 86720652, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-{3-[2,6-dichloro-4-(hydroxymethyl)benzoyl]-1H-pyrrolo[2,3-c]pyridin-7-yl}cyclopropanecarboxamide (900 mg, 2.23 mmol) in dichloromethane and carbon tetrachloride (2:1) at 0° C., phosphorus tribromide (1200 mg, 0.42 mL, 4.455 mmol) was added drop wise over a period of few minutes, stirred the mixture at 0° C. to room temperature. On completion, the reaction was quenched by adding saturated solution of sodium bicarbonate and extracted with dichloromethane. Organic layer was separated, washed with brine, dried over sodium sulfate and concentrated under vacuum. Purification by silica gel (100-200) column chromatography using dichloromethane and methanol gradient as eluent afforded N-{3-[4-(bromomethyl)-2,6-dichlorobenzoyl]-1H-pyrrolo[2,3-c]pyridin-7-yl}cyclopropanecarboxamide (330 mg, 33%).

Workup

  1. customOn completion, the reaction was quenched
  2. additionby adding saturated solution of sodium bicarbonate
  3. extractionextracted with dichloromethane
  4. customOrganic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customPurification by silica gel (100-200) column chromatography

Sources & evidence

ORD record
ord-ffc3b380eb034dcd8d0efef3e154ad57
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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