Carbon tetrabromide → HCID 67344867, compound

HRID 1846627Notes

Reaction equation

HRID 1846627 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:20][C:21]1[CH:22]=[C:23]([CH:46]=[CH:47][CH:48]=1)[C:24]([NH:26][C:27]1[C:28]([N:37]2[CH2:42][CH2:41][CH:40]([CH2:43][CH2:44]O)[CH2:39][CH2:38]2)=[N:29][CH:30]=[C:31]([S:33]([CH3:36])(=[O:35])=[O:34])[CH:32]=1)=[O:25].C(Br)(Br)(Br)[Br:50]>C(Cl)Cl>[Br:50][CH2:44][CH2:43][CH:40]1[CH2:41][CH2:42][N:37]([C:28]2[C:27]([NH:26][C:24](=[O:25])[C:23]3[CH:46]=[CH:47][CH:48]=[C:21]([Cl:20])[CH:22]=3)=[CH:32][C:31]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:30][N:29]=2)[CH2:38][CH2:39]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67322682HCID 67322682, compound

Product 1

HCID 67344867HCID 67344867, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 0.300 g (1.14 mmol) of triphenylphosphine, and 0.500 g (1.14 mmol) of 3-chloro-N-[4-(2-hydroxy-ethyl)-5′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-yl]benzamide in methylene chloride (20 mL), cooled to 0° C., is added 0.380 g (1.14 mmol) of carbon tetrabromide in multiple portions. The mixture is warmed to room temperature and stirred overnight then concentrated under reduced pressure and the residue purified by flash silica gel chromatography to provide 0.285 g (50% yield) of N-[4-(2-bromo-ethyl)-5′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-yl]-3-chloro-benzamide.

Workup

  1. temperatureThe mixture is warmed to room temperature
  2. concentrationthen concentrated under reduced pressure
  3. customthe residue purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-1f04bc175d0f436c9f933499ecf5c4b7
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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