Potassium Hydroxide → trans-(5-(2-chloropyridin-4-yl)-4,5-dihydrooxazol-4-yl)(2H-pyrrol-1(5H)-yl)methanone

HRID 1971277Notes

Reaction equation

HRID 1971277 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][N:3]=1.[OH-].[K+].[N+:12]([CH2:14][C:15]([N:17]1[CH2:21][CH:20]=[CH:19][CH2:18]1)=[O:16])#[C-:13]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([C@@H:8]2[O:9][CH:13]=[N:12][C@H:14]2[C:15]([N:17]2[CH2:21][CH:20]=[CH:19][CH2:18]2)=[O:16])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 27629942-Chloro-4-pyridinecarboxaldehyde2×HCID 575712512-Isocyano-1-(2H-pyrrol-1(5H)-yl)ethanone2×

Product 1

HCID 86626955trans-(5-(2-chloropyridin-4-yl)-4,5-dihydrooxazol-4-yl)(2H-pyrrol-1(5H)-yl)methanoneYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

SLA 07158 was prepared in accordance with method D using 2-chloropyridine-4-carbaldehyde SLA 07156 (0.47 g, 3.31 mmol), KOH (0.184 g, 3.33 mmol) in methanol (10 mL) and 2-Isocyano-1-(2H-pyrrol-1(5H)-yl)ethanone SLA 07178 (0.410 g, 3.01 mmol). The solution was stirred 2 h with continued cooling. After work-up and column chromatography on florisil (EtOAc), trans-(5-(2-chloropyridin-4-yl)-4,5-dihydrooxazol-4-yl)(2H-pyrrol-1(5H)-yl)methanone SLA 07158 was obtained as a yellow solid (0.597 g, 84%).

Workup

  1. customSLA 07158 was prepared in accordance with method D

Sources & evidence

ORD record
ord-d7dbca35862744bbbe3733725eea4162
Source dataset
uspto-grants-2013_04
Patent number
US08431599B2

Reaction notes

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