4-Pyridinecarboxaldehyde → trans-(4,5-dihydro-5-(pyridin-4-yl)oxazol-4-yl)(2H-pyrrol-1(5H)-yl)methanone

HRID 2065840Notes

Reaction equation

HRID 2065840 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[OH-].[K+].[N+:11]([CH2:13][C:14]([N:16]1[CH2:20][CH:19]=[CH:18][CH2:17]1)=[O:15])#[C-:12]>CO>[N:1]1[CH:6]=[CH:5][C:4]([C@@H:7]2[O:8][CH:12]=[N:11][C@H:13]2[C:14]([N:16]2[CH2:20][CH:19]=[CH:18][CH2:17]2)=[O:15])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 14797Potassium HydroxideHCID 575712512-Isocyano-1-(2H-pyrrol-1(5H)-yl)ethanone2×

Product 1

HCID 68954176trans-(4,5-dihydro-5-(pyridin-4-yl)oxazol-4-yl)(2H-pyrrol-1(5H)-yl)methanoneYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

SLA 07158 was prepared in accordance with method D using pyridine-4-carbaldehyde (0.293 mL, 2.40 mmol), KOH (0.13 g, 2.32 mmol) in methanol (10 mL) and 2-isocyano-1-(2H-pyrrol-1(5H)-yl)ethanone SLA 07178 (0.301 g, 2.20 mmol). The solution was stirred 2 h with continued cooling. After work-up and column chromatography on florisil (EtOAc), trans-(4,5-dihydro-5-(pyridin-4-yl)oxazol-4-yl)(2H-pyrrol-1(5H)-yl)methanone SLA 07180 was obtained (0.284 g, 53% yield) as a yellow oil.

Workup

  1. customSLA 07158 was prepared in accordance with method D

Sources & evidence

ORD record
ord-b5b91e2612c5449a875d7e01d45a26b4
Source dataset
uspto-grants-2012_10
Patent number
US08288556B2

Reaction notes

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