Water → Methyl 2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-4-(prop-2-en-1-yloxy)-1,3-thiazole-5-carboxylate

HRID 2282195Notes

Reaction equation

HRID 2282195 reaction equation
[OH:1][C:2]1[N:3]=[C:4]([C:11]2[C:12]([CH3:20])=[N:13][N:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=23)[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH:29]=[CH2:30].O>CN(C)C=O.C(OCC)(=O)C>[CH3:20][C:12]1[C:11]([C:4]2[S:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:2]([O:1][CH2:30][CH:29]=[CH2:28])[N:3]=2)=[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]2[N:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 136376955Methyl 4-hydroxy-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylate

Product 1

HCID 66855080Methyl 2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-4-(prop-2-en-1-yloxy)-1,3-thiazole-5-carboxylateYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-hydroxy-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylate (1.0 g, 3.5 mmol) produced in Example 13-B(i) was dissolved in N,N-dimethylformamide (50 mL), potassium carbonate (3.2 g, 9.7 mmol) and 3-bromoprop-1-ene (2.8 g, 23 mmol) were added, and the mixture was stirred at room temperature for 2 hr. Water (100 mL) and ethyl acetate (100 mL) were added to the reaction solution, and the mixture was stirred for 30 min. The organic layer was washed with water (100 mL×3) and saturated brine (10 mL) and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→0/100) to give the title compound (760 mg, 67%) as a brown solid.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. washThe organic layer was washed with water (100 mL×3) and saturated brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→0/100)

Sources & evidence

ORD record
ord-11613d40c3f645869eaa9b4f79439ffc
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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