Boron tribromide → HCID 76901620, compound

HRID 878509Notes

Reaction equation

HRID 878509 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:13]([C:14]3[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[CH:17]=[CH:16][N:15]=3)[N:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[N:13]([C:14]3[CH:19]=[C:18]([CH:17]=[CH:16][N:15]=3)[C:20]([OH:22])=[O:21])[N:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86725490HCID 86725490, compound

Product 1

HCID 76901620HCID 76901620, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
45 °C

Procedure

To a solution of 2-[5-(3-methoxyphenyl)-1H-pyrazol-1-yl]pyridine-4-carboxylic acid (160 mg, 0.54 mmol) in CH2Cl2 (5 mL) was added 1 M BBr3 in CH2Cl2 (5 mL) at 0° C., then stirred at 45° C. overnight. The reaction mixture was cooled, concentrated and dissolved with EtOAc, then washed with water and brine. The organic phase was dried, concentrated and purified by prep-HPLC to give the title compound (54 mg, 35%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 6.60-6.65 (3H, m), 6.71 (1H, dd, J=8.4, 2.0 Hz), 7.11 (1H, t, J=8.0 Hz), 7.78-7.82 (2H, m), 8.04(1H, s), 8.48 (1H, d, J=5.2 Hz), 9.46 (1H, s), 13.93 (1H, br s). [M+H] Calc'd for C15H11N3O3, 282; Found, 282.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. dissolutiondissolved with EtOAc
  4. washwashed with water and brine
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-270f7cc871584b1785745fab964d90ba
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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