Dichloromethane → HCID 178515835, compound

HRID 2184038Notes

Reaction equation

HRID 2184038 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]([C:17]([F:20])([F:19])[F:18])=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[C:21]1[CH:22]=[N:23][C:24]([O:27]C)=[CH:25][CH:26]=1.B(Br)(Br)Br.ClCCl>O1CCOCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([C:17]([F:20])([F:18])[F:19])=[N:16][C:11]3=[N:10][CH:9]=2)=[CH:4][C:3]=1[C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[N:23][CH:22]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 10110808HCID 10110808, compound

Product 1

HCID 178515835HCID 178515835, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-[4-fluoro-3-(6-methoxypyridin-3-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine (30 mg, 0.077 mmol) in 1,4-dioxane (2 ml) was treated with a 1M solution of boron tribromide in dichloromethane (0.77 ml, 0.77 mmol) and heated at reflux for 72 h. The mixture was partitioned between dichloromethane and water and the aqueous layer adjusted to pH 7. The organic layer was separated, washed with brine, dried (MgSO4), and concentrated in vacuo. 5-[2-Fluoro-5-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)phenyl]pyridin-2-ol was obtained in 31% yield after purification on silica gel: δH (400 MHz, DMSO) 6.46 (1H, d, J 9), 7.48-7.55 (2H, m), 7.72 (1H, ddd, J 8, 5 and 2), 7.76-7.82 (1H, m), 7.90 (1H, dd, J 8 and 2), 8.30 (1H, s), 9.35 (1H, d, J 7), 11.97 (1H, br); m/z (ES+) 375 (M++H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 72 h
  3. customThe mixture was partitioned between dichloromethane and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6da3fd892274e1b8865bab06225de4d
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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