Phosphorus tribromide → HCID 136146128, compound

HRID 341185Notes

Reaction equation

HRID 341185 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]3[C:15]([C:18]4[CH:19]=[C:20]([NH:24][C:25]([NH:27][CH2:28][C:29]([F:32])([F:31])[F:30])=[O:26])[CH:21]=[CH:22][CH:23]=4)=[CH:16][N:17]=[C:11]3[CH:10]=2)=[CH:5][CH:4]=1.P(Br)(Br)Br>ClCCCl>[O:2]=[C:3]1[NH:8][CH:7]=[C:6]([C:9]2[CH:14]=[CH:13][N:12]3[C:15]([C:18]4[CH:19]=[C:20]([NH:24][C:25]([NH:27][CH2:28][C:29]([F:30])([F:31])[F:32])=[O:26])[CH:21]=[CH:22][CH:23]=4)=[CH:16][N:17]=[C:11]3[CH:10]=2)[CH:5]=[CH:4]1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 59320812HCID 59320812, compound

Product 1

HCID 136146128HCID 136146128, compoundYield 124.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To 1-{3-[7-(6-Methoxy-pyridin-3-yl)-imidazo[1,2-a]pyridin-3-yl]-phenyl}-3-(2,2,2-trifluoro-ethyl)-urea (0.187 g, 0.226 mmol) in DCE (10 ml) was added PBr3 (0.174 ml). The reaction was heated at 80° C. for 3 hours, then partitioned between EtOAc and water, insoluble material filtered off and dried to give 1-{3-[7-(6-Oxo-1,6-dihydro-pyridin-3-yl)-imidazo[1,2-a]pyridin-3-yl]-phenyl}-3-(2,2,2-trifluoro-ethyl)-urea (0.12 g) MS: [M+H]+428

Workup

  1. custompartitioned between EtOAc and water, insoluble material
  2. filtrationfiltered off
  3. customdried

Sources & evidence

ORD record
ord-7af9126c85aa4a13af17073150c936aa
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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