Triphenylphosphine → 2-[3-(5-Amino-3-tert-butyl-pyrazol-1-yl)-phenoxy]-ethanol

HRID 2285311Notes

Reaction equation

HRID 2285311 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2O)[N:5]=[C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCCC1[O:43][CH2:44][CH2:45][OH:46].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[C:11]([CH:10]=[CH:9][CH:8]=2)[O:43][CH2:44][CH2:45][OH:46])[N:5]=[C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 41668332-(Oxan-2-yloxy)ethan-1-olHCID 5363146Diisopropyl azodicarboxylateHCID 587052255-Amino-3-tert-butyl-pyrazol-1-yl-phenol

Product 1

HCID 591518232-[3-(5-Amino-3-tert-butyl-pyrazol-1-yl)-phenoxy]-ethanolYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Intermediate 95a (1.2 g, 5.2 mmol) and triphenyl phosphine (2.72 g, 10.4 mmol) in THF (30 mL), under an atmosphere of argon was treated with 2-(tetrahydro-pyran-2-yloxy)-ethanol (1.05 mL, 7.78 mmol), followed by the dropwise addition of diisopropylazodicarboxylate (1.64 mL, 10.4 mmol). The reaction mixture was then stirred at RT for 1 h. The reaction mixture was eluted on a SCX-2 cartridge using MeOH and 2M NH3 in MeOH. The basic fractions were evaporated under reduced pressure and the product was purified by FCC, using EtOAc/DCM 0-60% to afford the title compound as a brown gum (1.0 g, 80%). LCMS (Method 3): Rt 2.27 min, m/z 276 [MH+].

Workup

  1. washThe reaction mixture was eluted on a SCX-2 cartridge
  2. customThe basic fractions were evaporated under reduced pressure
  3. customthe product was purified by FCC

Sources & evidence

ORD record
ord-dc126005c1104d1dbc938c6cbfb246fc
Source dataset
uspto-grants-2015_09
Patent number
US09145413B2

Reaction notes

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