4-Hydroxymethylpyridine → HCID 67294068, compound

HRID 517968Notes

Reaction equation

HRID 517968 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:32]1[CH:37]=[CH:36][C:35]([CH2:38]O)=[CH:34][CH:33]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCOCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:38][C:35]2[CH:36]=[CH:37][N:32]=[CH:33][CH:34]=2)=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:3]=1

Participants

6

Reactant 4

HCID 114724-HydroxymethylpyridineHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 142784o-Cresol, 4-bromo-alpha,alpha,alpha-trifluoro-

Product 1

HCID 67294068HCID 67294068, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of 4-bromo-2-(trifluoromethyl)phenol (8.00 g) in 1,4-dioxane (100 ml), triphenylphosphine (10.99 g) and 4-pyridylcarbinol (3.84 g) were added. Then diisopropyl azodicarboxylate (8.93 g) was dropwised and stirred at 20° C. for 18 h. The mixture was evaporated off the solvent, diethyl ether (100 ml) and iso-hexane (25 ml) were added and stirred at 20° C. for 2 h, stood for 3 days, filtered and washed with diethyl ether and iso-hexane. The filtrate was concentrated and purified by Biotage SNAP cartridge KP-Sil column (100 g, heptane:ethyl acetate=1:0, 2:1 to 1:1) to give 11.16 g red-orange oil as 4-((4-bromo-2-(trifluoromethyl)phenoxy)methyl)-pyridine (80% purity).

Workup

  1. additionwere added
  2. customThe mixture was evaporated off the solvent, diethyl ether (100 ml) and iso-hexane (25 ml)
  3. additionwere added
  4. stirringstirred at 20° C. for 2 h
  5. waitstood for 3 days
  6. filtrationfiltered
  7. washwashed with diethyl ether and iso-hexane
  8. concentrationThe filtrate was concentrated
  9. custompurified by Biotage SNAP cartridge KP-Sil column (100 g, heptane:ethyl acetate=1:0, 2:1 to 1:1)

Sources & evidence

ORD record
ord-16271858e81a418d826958e34c73a5ac
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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