Methanol → HCID 178498428, compound

HRID 514443Notes

Reaction equation

HRID 514443 reaction equation
BrC1C=CC(C[O:7][C:8]2[N:12]([C:13]3[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=[CH:15][N:14]=3)[N:11]=[CH:10][CH:9]=2)=CC=1.B(Br)(Br)Br.CO.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:7][C:8]1[N:12]([C:13]2[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=[CH:15][N:14]=2)[N:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 86725564Methyl 2-{5-[(4-bromobenzyl)oxy]-1H-pyrazol-1-yl}pyridine-4-carboxylate

Product 1

HCID 178498428HCID 178498428, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of methyl 2-{5-[(4-bromobenzyl)oxy]-1H-pyrazol-1-yl}pyridine-4-carboxylate (765 mg, 1.97 mmol, EXAMPLE 68) in DCM (8 mL) was purged with nitrogen and cooled to −78° C. BBr3 (6 mL, 5.93 mmol, 1M in DCM) was added at this temperature. Thereto, the mixture was stirred at the same temperature for an hour, methanol was added until no gas released, and then the above mixture was basified with NaHCO3 aq (pH=3). Extracted with ethylacetate three times, and the organic phase was washed with brine and dried with Na2SO4, concentrated and the residue was washed with ethylacetate to give 260 mg of the title compound (60%). 1H NMR (400 MHz, CD3OD): δ 4.02 (3H, s), 7.91-7.97 (2H, m), 8.69-8.70 (2H, m). [M+H] Calc'd for C10H9N3O3, 220. Found, 220.

Workup

  1. extractionExtracted with ethylacetate three times
  2. washthe organic phase was washed with brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. washthe residue was washed with ethylacetate

Sources & evidence

ORD record
ord-cb52190e27314b3fad7f308c82defa34
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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