Carbon tetrabromide → HCID 67340945, compound

HRID 1846620Notes

Reaction equation

HRID 1846620 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[C:5]([NH:7][C:8]1[C:9]([N:15]2[CH2:20][CH2:19][CH:18]([CH:21](O)C)[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:47]>C(Cl)Cl>[Br:47][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:24]=[CH:25][CH:26]=[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 67340994HCID 67340994, compound

Product 1

HCID 67340945HCID 67340945, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.170 g (0.431 mmol) of 3-chloro-N-[5′-chloro-4-(1-hydroxy-ethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-yl]-benzamide and 0.135 g (0.517 mmol) of triphenylphosphine in methylene chloride (15 mL) is stirred under an atmosphere of nitrogen at 0 C for 5 minutes. To this is added 0.171 g (0.517 mmol) of carbon tetrabromide in several portions. The mixture is stirred at 0 C for 30 minutes and then warmed to room temperature and stirred for 2 days. The mixture is concentrated under reduced pressure and purified by flash silica gel chromatography to give 0.030 g (15%) of N-(4-bromomethyl-5′-chloro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-yl)-3-chloro-benzamide as a colorless oil.

Workup

  1. stirringThe mixture is stirred at 0 C for 30 minutes
  2. stirringstirred for 2 days
  3. concentrationThe mixture is concentrated under reduced pressure
  4. custompurified by flash silica gel chromatography

Sources & evidence

ORD record
ord-de5e0230d26f482fb47c34af52034bc4
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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