Triphenylphosphine → 1-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-((5-(trifluoromethyl)-3-thienyl)methoxy)pyridin-2(1H)-one

HRID 2203092Notes

Reaction equation

HRID 2203092 reaction equation
[CH2:1]([C:3]1[N:7]([CH3:8])[C:6]2[CH:9]=[C:10]([N:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]3=[O:20])[CH:11]=[CH:12][C:5]=2[N:4]=1)[CH3:2].[F:21][C:22]([F:31])([F:30])[C:23]1[S:27][CH:26]=[C:25]([CH2:28]O)[CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCCOC)=O)=NC(OCCOC)=O>C1COCC1.O>[CH2:1]([C:3]1[N:7]([CH3:8])[C:6]2[CH:9]=[C:10]([N:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:28][C:25]4[CH:24]=[C:23]([C:22]([F:31])([F:30])[F:21])[S:27][CH:26]=4)=[CH:15][C:14]3=[O:20])[CH:11]=[CH:12][C:5]=2[N:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 199573935-(Trifluoromethyl)-3-thiophenemethanolHCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamateHCID 896909981-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one

Product 1

HCID 896911051-(2-Ethyl-1-methyl-1H-benzimidazol-6-yl)-4-((5-(trifluoromethyl)-3-thienyl)methoxy)pyridin-2(1H)-oneYield 14.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-ethyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one (300 mg), (5-(trifluoromethyl)-3-thienyl)methanol (352 mg) and triphenylphosphine (877 mg) in THF (10 ml) was added bis(2-methoxyethyl) azodicarboxylate (783 mg), and the mixture was stirred at room temperature for 3 h. The mixture was poured into water and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, concentrated and purified by silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH). The resulting solid was recrystallized from IPA-IPE to give the title compound (70.0 mg) as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (hexane/EtOAc
  6. customThe resulting solid was recrystallized from IPA-IPE

Sources & evidence

ORD record
ord-e6b4d7188faa4b1e829239c5ffe2c4f7
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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