Water → 1-[5-(difluoromethyl)pyridin-2-yl]-1H-pyrrole-3-carboxylic acid tert-butyl ester

HRID 1748477Notes

Reaction equation

HRID 1748477 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([C:10]1[CH:14]=[CH:13][NH:12][CH:11]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].Br[C:16]1[CH:21]=[CH:20][C:19]([CH:22]([F:24])[F:23])=[CH:18][N:17]=1.O>CN(C)C=O>[C:3]([O:7][C:8]([C:10]1[CH:14]=[CH:13][N:12]([C:16]2[CH:21]=[CH:20][C:19]([CH:22]([F:24])[F:23])=[CH:18][N:17]=2)[CH:11]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11171190tert-butyl 1H-pyrrole-3-carboxylateHCID 547722752-Bromo-5-(difluoromethyl)pyridine

Product 1

HCID 866924421-[5-(difluoromethyl)pyridin-2-yl]-1H-pyrrole-3-carboxylic acid tert-butyl esterYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (230 mg) was added to a solution of 1H-pyrrole-3-carboxylic acid tert-butyl ester (804 mg) in N,N-dimethylformamide (9.6 ml) at room temperature and stirred at the same temperature for 0.5 hour. 2-Bromo-5-(difluoromethyl)pyridine (1.0 g) was added and stirred at 60° C. for an hour. After completion of the reaction, the reaction solution was cooled to room temperature, water was added and the precipitated solid was filtered. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1-[5-(difluoromethyl)pyridin-2-yl]-1H-pyrrole-3-carboxylic acid tert-butyl ester (1.01 g) as a white solid.

Workup

  1. stirringstirred at 60° C. for an hour
  2. customAfter completion of the reaction
  3. filtrationthe precipitated solid was filtered
  4. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-28bafb48d49d4dc4b6579cae3148053e
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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