Carbon tetrabromide → HCID 67341717, compound

HRID 1846616Notes

Reaction equation

HRID 1846616 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[C:5]([NH:7][C:8]1[C:9]([N:15]2[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][CH2:23]O)[CH2:17][CH2:16]2)=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=1)=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:48]>C(Cl)Cl>[Br:48][CH2:23][CH2:22][CH2:21][CH:18]1[CH2:19][CH2:20][N:15]([C:9]2[C:8]([NH:7][C:5](=[O:6])[C:4]3[CH:25]=[CH:26][CH:27]=[C:2]([Cl:1])[CH:3]=3)=[CH:13][C:12]([Cl:14])=[CH:11][N:10]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67341654HCID 67341654, compound

Product 1

HCID 67341717HCID 67341717, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.080 g (0.20 mmol) of the above amide and 0.056 g (0.22 mmol) of triphenylphosphine in anhydrous methylene chloride (10 mL), under an atmosphere of nitrogen, is stirred at room temperature for 20 minutes. To this mixture is added 0.071 g (0.22 mmol) of carbon tetrabromide and the resulting mixture is stirred overnight at room temperature. The reaction mixture is concentrated under reduced pressure and the residue is purified by flash silica gel chromatography to give 0.037 g (40%) of N-[4-(3-bromo-propyl)-5′-chloro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-yl]-3-chloro-benzamide.

Workup

  1. stirringthe resulting mixture is stirred overnight at room temperature
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. customthe residue is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-6e6ca26266c34cf78f728bf1c2c50e5d
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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