Triphenylphosphine → 6-((1-(4-Fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)methoxy)-2-isopropyl-1H-pyrrolo[3,4-c]pyridin-3(2H)-one

HRID 402454Notes

Reaction equation

HRID 402454 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][OH:14])=[C:11]([CH3:15])[N:10]=[N:9]2)=[CH:4][CH:3]=1.O[C:17]1[N:22]=[CH:21][C:20]2[C:23](=[O:29])[N:24]([CH:26]([CH3:28])[CH3:27])[CH2:25][C:19]=2[CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH2:13][O:14][C:17]3[N:22]=[CH:21][C:20]4[C:23](=[O:29])[N:24]([CH:26]([CH3:27])[CH3:28])[CH2:25][C:19]=4[CH:18]=3)=[C:11]([CH3:15])[N:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19914681(1-(4-Fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)methanolHCID 178456170HCID 178456170, compound

Product 1

HCID 573358346-((1-(4-Fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)methoxy)-2-isopropyl-1H-pyrrolo[3,4-c]pyridin-3(2H)-oneYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3-(4-fluoro-phenyl)-5-methyl-3H-[1,2,3]triazol-4-yl]-methanol (251 mg, 1.21 mmol) in THF (30 mL) was added 6-hydroxy-2-isopropyl-1H-pyrrolo[3,4-c]pyridin-3(2H)-one (232 mg, 1.21 mmol) and triphenylphosphine (413 mg, 1.58 mmol) at ambient temperature under an argon atmosphere. Then diethyl azodicarboxylate (624 μL, 1.58 mmol) was added and the reaction mixture was stirred for 72 h at room temperature. Concentration and purification by chromatography (silica, 20 to 50% ethyl acetate in heptane) afforded the title compound (141 mg, 31%) as a white solid. MS: m/e=382.2 [M+H]+.

Workup

  1. concentrationConcentration and purification by chromatography (silica, 20 to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-6d22af06452f45e0af22d35b106d393b
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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