Potassium Carbonate → HCID 89633279, compound

HRID 1525675Notes

Reaction equation

HRID 1525675 reaction equation
Br[CH2:2][C:3]1[C:15]([Cl:16])=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[C:5]([F:17])[CH:4]=1.[Cl:18][C:19]1[CH:20]=[C:21]([OH:28])[CH:22]=[N:23][C:24]=1[CH:25]1[CH2:27][CH2:26]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Cl:16][C:15]1[C:3]([CH2:2][O:28][C:21]2[CH:22]=[N:23][C:24]([CH:25]3[CH2:27][CH2:26]3)=[C:19]([Cl:18])[CH:20]=2)=[CH:4][C:5]([F:17])=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 580424875-Chloro-6-cyclopropylpyridin-3-OLHCID 86702928HCID 86702928, compound

Product 1

HCID 89633279HCID 89633279, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of tert-butyl 4-(bromomethyl)-5-chloro-2-fluorobenzoate (Preparation 25, 2.50 g, 7.99 mmol) and 5-chloro-6-cyclopropylpyridin-3-ol (Preparation 42 WO2012007869, 1.13 g, 6.66 mmol) in DMSO (25 mL) was added K2CO3 (2.76 g, 19.9 mmol). The resulting mixture was stirred under nitrogen at room temperature for 18 hours. The reaction mixture was then quenched with water (30 mL) and extracted with EtOAc (2×30 mL). The combined organic layers were washed with water (30 mL), dried over MgSO4 and evaporated under reduced pressure to give the crude product (2.69 g). Purification was accomplished by column chromatography on silica (eluting with 1:9 Et2O/cyclohexane) affording the title compound (1.24 g, 46%).

Workup

  1. customThe reaction mixture was then quenched with water (30 mL)
  2. extractionextracted with EtOAc (2×30 mL)
  3. washThe combined organic layers were washed with water (30 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customto give the crude product (2.69 g)
  7. customPurification

Sources & evidence

ORD record
ord-04f09de6b24243349d62b830e463d726
Source dataset
uspto-grants-2015_07
Patent number
US09085517B2

Reaction notes

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