Boron Trichloride → HCID 178516309, compound

HRID 1433152Notes

Reaction equation

HRID 1433152 reaction equation
B(Cl)(Cl)Cl.C(OC([N:12]1[CH2:17][CH2:16][N:15]([C:18]2[C:19]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=3[O:30]CC3C=CC=CC=3)=[N:20][NH:21][CH:22]=2)[CH2:14][CH2:13]1)=O)(C)(C)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:19]2[C:18]([N:15]3[CH2:16][CH2:17][NH:12][CH2:13][CH2:14]3)=[CH:22][NH:21][N:20]=2)=[C:24]([OH:30])[CH:25]=1

Participants

5

Reactant 3

HCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 178452253HCID 178452253, compound

Product 1

HCID 178516309HCID 178516309, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trichloride (1.0 M in DCM; 0.829 mL, 0.829 mmol) was added to a solution of 4-[3-(2-benzyloxy-4-fluoro-phenyl)-1H-pyrazol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (75 mg, 0.166 mmol) in DCM (7.5 mL). A brown precipitate formed. The mixture was stirred at room temperature for 1 hour and then poured into saturated aqueous sodium bicarbonate (50 mL) and extracted with DCM (3×50 mL). The combined organic layers were dried (MgSO4) and the solvents removed in vacuo. The product was purified by preparative HPLC to give 3-(4-fluoro-2-hydroxyphenyl)4(piperazin-1-yl)-1H-pyrazole (13 mg, 30%) as an off-white solid; δH (MeOH-d4) 7.96 (1H, br s), 7.72 (1H, s), 6.71-6.64 (2H, m), 3.36-3.33 (4H, m), 3.13-3.10 (4H, m), 2.65 (1H, s); LCMS retention time 1.46 min, M+H+ 263.2.

Workup

  1. customA brown precipitate formed
  2. extractionextracted with DCM (3×50 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customthe solvents removed in vacuo
  5. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-a83207cde49f4a9cb45fe1413f9b95e6
Source dataset
uspto-grants-2009_11
Patent number
US07612201B2

Reaction notes

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