Triphenylphosphine → HCID 86720582, compound

HRID 513215Notes

Reaction equation

HRID 513215 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH2:15][CH2:16][OH:17])=[C:9]([C:11]([O:13][CH3:14])=[O:12])[N:10]=2)[CH:5]=[CH:6][N:7]=1.[F:18][C:19]([F:29])([F:28])[O:20][C:21]1[CH:26]=[CH:25][C:24](O)=[CH:23][CH:22]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH2:15][CH2:16][O:17][C:24]3[CH:23]=[CH:22][C:21]([O:20][C:19]([F:18])([F:28])[F:29])=[CH:26][CH:25]=3)=[C:9]([C:11]([O:13][CH3:14])=[O:12])[N:10]=2)[CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 70015p-(Trifluoromethoxy)phenolHCID 5363146Diisopropyl azodicarboxylateHCID 86720583HCID 86720583, compound

Product 1

HCID 86720582HCID 86720582, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of methyl 8-chloro-3-(2-hydroxyethyl)imidazo[1,2-a]pyrazine-2-carboxylate (18 mg, 0.070 mmol) in toluene (1 mL) was added 4-trifluoromethoxyphenol (0.014 mL, 0.106 mmol), Ph3P (27.7 mg, 0.106 mmol), and DIAD (0.021 mL, 0.106 mmol). After 30 min, the reaction was concentrated in vacuo and then purified on silica (gradient elution, 0-100% EtOAc/hexanes) to yield the title product (10 mg). HRMS (ESI) calc (M+H)+=416.0619. found 416.0616.

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. custompurified on silica (gradient elution, 0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-64ea445ded69406ba78f71ae234a306f
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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