Boron tribromide → HCID 136041870, compound

HRID 1466584Notes

Reaction equation

HRID 1466584 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:26]C)=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([CH3:25])[N:9]=2)[CH:7]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:26])=[C:6]([C:8]2[C:12]([NH:13][C:14]([C:16]3[CH:17]=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[N:21][C:20]=34)=[O:15])=[CH:11][N:10]([CH3:25])[N:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 49856845HCID 49856845, compound

Product 1

HCID 136041870HCID 136041870, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(3-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (synthesized following the procedures described for Example 14) (193.9 mg, 0.5065 mmol) in 8.0 mL dichloromethane was added boron tribromide (1.50 mL of a 1.0M solution in dichloromethane, 1.5 mmol). The reaction was stirred at room temperature for 1 hour. The reaction was then quenched with 1 mL methanol, diluted with ethyl acetate, and washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, and concentrated to give 191.5 mg (100%) of N-(3-(5-chloro-2-hydroxyphenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide, which was carried forward without purification. LCMS (ESI) m+H=369.1.

Workup

  1. customThe reaction was then quenched with 1 mL methanol
  2. additiondiluted with ethyl acetate
  3. washwashed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5bc1c05bc86e4f3a8eb0f3a7a8b8babf
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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