Hydrogen Bromide → HCID 86656434, compound

HRID 1895887Notes

Reaction equation

HRID 1895887 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[CH:12][C:13]3[N:14]([N:16]=[CH:17][C:18]=3[C:19](=[O:21])[CH3:20])[CH:15]=2)=[CH:6][CH:5]=1.Br.ClCCl>CC(O)=O>[Br:1][CH2:20][C:19]([C:18]1[CH:17]=[N:16][N:14]2[CH:15]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=3)[CH:11]=[CH:12][C:13]=12)=[O:21]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 6344DichloromethaneHCID 24408BromineHCID 67350153HCID 67350153, compound

Product 1

HCID 86656434HCID 86656434, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (57.9 μL, 1.13 mmol) was added to a solution of 1-[6-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-3-yl]ethanone (8, 197 mg, 0.775 mmol) in AcOH (1 mL) and hydrobromic acid (88 μL, 0.775 mmol). The reaction was heated to 50° C. for 2 hours after which an aqueous solution of 10% Na2S2SO3 (5 mL) and dichloromethane (10 mL) were added to the reaction. The organic was collected and washed with a saturated solution of sodium bicarbonate (10 mL), dried over sodium sulfate and concentrated. The reaction was purified by column chromatography (10% acetone in hexanes) to yield 2-bromo-1-[6-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-3-yl]ethanone (9, 220.4 mg, 0.662 mmol, 85% yield). MS APCI: [M+H]+ m/z 334.2.

Workup

  1. additionwere added to the reaction
  2. customThe organic was collected
  3. washwashed with a saturated solution of sodium bicarbonate (10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe reaction was purified by column chromatography (10% acetone in hexanes)

Sources & evidence

ORD record
ord-dbc596d80a904539ba0e2c1bd9bfbcc4
Source dataset
uspto-grants-2013_08
Patent number
US08518911B2

Reaction notes

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