1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-[-2-(5,8-Dimethyl[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-vinyl]-5H-imidazo[2,1-a]isoindole

HRID 2401520Notes

Reaction equation

HRID 2401520 reaction equation
[N:1]1[C:2]([CH:13]=O)=[CH:3][N:4]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=12.[Cl-].[CH3:16][C:17]1[N:22]2[N:23]=[C:24]([CH2:26][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:25]=[C:21]2[C:20]([CH3:46])=[N:19][CH:18]=1.N12CCCN=C1CCCCC2>C1COCC1>[CH3:16][C:17]1[N:22]2[N:23]=[C:24]([CH:26]=[CH:13][C:2]3[N:1]=[C:5]4[C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[CH2:12][N:4]4[CH:3]=3)[N:25]=[C:21]2[C:20]([CH3:46])=[N:19][CH:18]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 222245345H-Imidazo[2,1-a]isoindole-2-carbaldehydeHCID 86665503((5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)methyl)triphenylphosphonium chloride

Product 1

HCID 696708672-[-2-(5,8-Dimethyl[1,2,4]triazolo[1,5-a]pyrazin-2-yl)-vinyl]-5H-imidazo[2,1-a]isoindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5H-Imidazo[2,1-a]isoindole-2-carbaldehyde (150 mg, 0.81 mmol) in dry THF (5.3 mL) was added to (5,8-Dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-ylmethyl)-triphenyl-phosphonium chloride (374 mg, 0.81 mmol) under argon and 1,8-diazabicyclo[5.4.0]undec-7-ene (120 micro L, 0.81 mmol) was added. The reaction mixture was stirred at room temperature for 12 hours after which it was evaporated onto silica gel (2 g). Silica gel chromatography (gradient elution; A:B 100:0 to 0:100, where A is ethyl acetate and B is 10% MeOH in ethyl acetate) afforded the title compound as a mixture of the cis and trans isomers (139 mg, 52%). LC-MS: m/z=329.3 (MH+), tR=0.96 minutes.

Workup

  1. customwas evaporated onto silica gel (2 g)
  2. washSilica gel chromatography (gradient elution

Sources & evidence

ORD record
ord-d15195b7a2f04e5693e0f974617a9864
Source dataset
uspto-grants-2014_08
Patent number
US08796304B2

Reaction notes

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