Carbon tetrabromide → HCID 69708935, compound

HRID 2183926Notes

Reaction equation

HRID 2183926 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([CH2:17]O)=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[C:19]1[C:20]([C:25]#[N:26])=[CH:21][CH:22]=[CH:23][CH:24]=1.C(Br)(Br)(Br)[Br:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:28][CH2:17][C:15]1[CH:14]=[CH:13][N:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:19]4[C:20]([C:25]#[N:26])=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:4]=3)=[CH:9][N:10]=[C:11]2[N:16]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 10291184HCID 10291184, compound

Product 1

HCID 69708935HCID 69708935, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2′-fluoro-5′-(7-hydroxymethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile (100 mg, 0.291 mmol) in dichloromethane (5 ml) was added carbon tetrabromide (289 mg, 0.872 mmol) and polymer-supported triphenylphosphine (291 mg, 0.872 mmol). This mixture was stirred at ambient temperature for 1 h followed by removal of the polymer by filtration. N,N-Dimethylformamide (5 ml) was added to the reaction mixture and dichloromethane removed by evaporation under vacuum without heating to give 5′-(7-bromomethylimidazo[1,2-α]pyrimidin-3-yl)-2′-fluorobiphenyl-2-carbonitrile as a solution in N,N-dimethylformamide.

Workup

  1. customfollowed by removal of the polymer by filtration
  2. additionN,N-Dimethylformamide (5 ml) was added to the reaction mixture and dichloromethane
  3. customremoved by evaporation under vacuum
  4. temperaturewithout heating

Sources & evidence

ORD record
ord-0834d900dbfa4c71a0fa1cbe9c81ac60
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

Loading…