Boron tribromide → HCID 57580517, compound

HRID 1692432Notes

Reaction equation

HRID 1692432 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)[CH:6]=[C:7]([CH3:22])[C:8]=1[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:13][CH2:12]1)=[O:10].B(Br)(Br)Br.C(=O)([O-])O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)[CH:6]=[C:7]([CH3:22])[C:8]=1[C:9]([N:11]1[CH2:12][CH2:13][CH:14]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:15][CH2:16]1)=[O:10]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 57580553HCID 57580553, compound

Product 1

HCID 57580517HCID 57580517, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.51 g (1.1 mmol) of (3-methoxy-5-methyl-3′-trifluoromethyl-biphenyl-4-yl)-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 44) in 15 ml of CH2Cl2 was added at 0° C. 0.39 ml=0.57 g (2.3 mmol) of a boron tribromide solution (1.0 molar in CH2Cl2) drop by drop and the reaction mixture was the warmed up to RT. After 4 hours, it was poured into crashed ice, neutralized with sodium hydrogen carbonate solution and extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1) to give 0.18 g (36%) of the title compound as colorless amorphous solid. MS: 433.2 (MH+).

Workup

  1. additionit was poured
  2. extractionextracted twice with CH2Cl2
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1)

Sources & evidence

ORD record
ord-ed981975674c4c43b8f071013d8cb2ed
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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