Cyclopropanemethanol → HCID 67505007, compound

HRID 1929894Notes

Reaction equation

HRID 1929894 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:14])=[N:8][C:9](Cl)=[C:10]([Br:12])[CH:11]=1)=[O:5])[CH3:2].[OH:15][CH2:16][CH:17]1[CH2:19][CH2:18]1.C1CCN2C(=NCCC2)CC1>>[CH2:1]([O:3][C:4](=[O:5])[C:6]1[CH:11]=[C:10]([Br:12])[C:9]([O:15][CH2:16][CH:17]2[CH2:19][CH2:18]2)=[N:8][C:7]=1[CH3:14])[CH3:2]

Participants

4

Reactant 3

HCID 75644CyclopropanemethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86619573Ethyl 5-bromo-6-chloro-2-methyl-3-pyridinecarboxylate

Product 1

HCID 67505007HCID 67505007, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-6-chloro-2-methyl-3-pyridinecarboxylic acid ethyl ester (CAN 41598-77-0) (0.7 g, 2.5 mmol), hydroxymethylcyclopropane (0.57 mL, 6.2 mmol) and DBU (0.94 mL) was heated for 15 min in a microwave oven to 100° C. The reaction mixture was cooled to room temperature and partitioned between 10% citric acid and ethyl acetate. The phases were separated and the organic phase was purified by chromatography on silica gel with a cyclohexane:ethyl acetate gradient to yield the title compound as light yellow solid, MS (ISP) 314.0, 316.0 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between 10% citric acid and ethyl acetate
  3. customThe phases were separated
  4. customthe organic phase was purified by chromatography on silica gel with a cyclohexane

Sources & evidence

ORD record
ord-d94f77b653eb4b6aba2c9a8625cb3cfe
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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