2,6-Lutidine → HCID 67112149, compound

HRID 540790Notes

Reaction equation

HRID 540790 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[N:10]([CH2:24][CH2:25][OH:26])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.N1C(C)=CC=CC=1C.O([Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])S(C(F)(F)F)(=O)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[C:11]([O:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:18][CH:19]=3)[N:10]([CH2:24][CH2:25][O:26][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 67111088HCID 67111088, compound

Product 1

HCID 67112149HCID 67112149, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 2-{3-(3-bromophenyl)-5-[4-(trifluoromethyl)phenoxy]-1H-pyrazol-1-yl}ethanol (7.6 g, 18 mmol) and 2,6-lutidine (6.2 mL, 53 mmol) in 40 mL of CH2Cl2 under an argon atmosphere was cooled in an ice bath. TBDMS triflate (7.1 g, 27 mmol) was added dropwise and the mixture was stirred for 30 min. The mixture was diluted with CH2Cl2 and washed with saturated aqueous NaHCO3, water, brine, then dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. The residue was chromatographed on a 120 g silica gel column using 0-70% CHCl3:hexanes over 40 min at 85 mL/min. The product-containing fractions were combined and the solvent was removed under reduced pressure to give 2-{3-(3-bromophenyl)-5-[4-(trifluoromethyl)phenoxy]-1H-pyrazol-1-yl}-1-(tert-butyldimethylsilyloxy)ethane as an oil. Calcd (M+1)+: 542.5. Found: 542.8

Workup

  1. washwashed with saturated aqueous NaHCO3, water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customThe residue was chromatographed on a 120 g silica gel column
  6. waithexanes over 40 min at 85 mL/min
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-99c757b2776040dc96e2a0269ab1f318
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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