Boron Trichloride → HCID 178488687, compound

HRID 1296943Notes

Reaction equation

HRID 1296943 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([F:15])[C:12]([Cl:16])=[CH:11][C:10]=1[C:17]1[N:21](COCC[Si](C)(C)C)[N:20]=[C:19]([CH3:30])[C:18]=1[C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>ClCCl>[Cl:16][C:12]1[C:13]([F:15])=[CH:14][C:9]([OH:8])=[C:10]([C:17]2[NH:21][N:20]=[C:19]([CH3:30])[C:18]=2[C:31]2[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2)[CH:11]=1

Participants

5

Reactant 3

HCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 58913529HCID 58913529, compound

Product 1

HCID 178488687HCID 178488687, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

5-(2-Benzyloxy-5-chloro-4-fluoro-phenyl)-4-(4-methoxy-phenyl)-3-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole (1 eq) was taken up in anhydrous dichloromethane and the solution was cooled under nitrogen to 0° C. 1M boron trichloride in dichloromethane (6 eq) was added dropwise and the solution was allowed to stir for 1 hour. The reaction mixture was added dropwise to sat. NaHCO3 (aq) and the resulting solution was extracted into dichloromethane. The organic phases were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by preparative LC/MS, to give 4-chloro-5-fluoro-2-[4-(4-methoxy-phenyl)-5-methyl-2H-pyrazol-3-yl]-phenol as a white solid.

Workup

  1. extractionthe resulting solution was extracted into dichloromethane
  2. washThe organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative LC/MS

Sources & evidence

ORD record
ord-ef8f3ee3afe949c7932d34e0359ce409
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

Loading…