Water → 5-Cyclopropyl-7-(2,6-difluorobenzyloxy)-2-methylpyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester

HRID 1486313Notes

Reaction equation

HRID 1486313 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:12][CH2:13][CH3:14])(=[O:11])[C:8]#[C:9][CH3:10].CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:28][N+:29]1[CH:34]=[CH:33][C:32]([CH:35]2[CH2:37][CH2:36]2)=[CH:31][C:30]=1[O:38][CH2:39][C:40]1[C:45]([F:46])=[CH:44][CH:43]=[CH:42][C:41]=1[F:47].O>CN(C=O)C>[CH2:13]([O:12][C:7]([C:8]1[C:9]([CH3:10])=[N:28][N:29]2[C:30]([O:38][CH2:39][C:40]3[C:45]([F:46])=[CH:44][CH:43]=[CH:42][C:41]=3[F:47])=[CH:31][C:32]([CH:35]3[CH2:37][CH2:36]3)=[CH:33][C:34]=12)=[O:11])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 78043Ethyl 2-butynoateHCID 1178578761-Amino-4-cyclopropyl-2-[(2,6-difluorobenzyl)oxy]pyridinium 2,4,6-trimethylbenzenesulphonate

Product 1

HCID 1178646895-Cyclopropyl-7-(2,6-difluorobenzyloxy)-2-methylpyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

468 mg (3.4 mmol) of potassium carbonate were added to a mixture of 264 μl (2.3 mmol) of ethyl but-2-ynoate and 540 mg (1.1 mmol) of 1-amino-4-cyclopropyl-2-[(2,6-difluorobenzyl)oxy]pyridinium 2,4,6-trimethylbenzenesulphonate (Example 147A) in 10 ml of DMF. The reaction mixture was stirred at room temperature for 2 h and then poured into 25 ml of water precooled to 5° C. The precipitate was filtered off, washed with water and dried.

Workup

  1. customprecooled to 5° C
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-1a085c75d1aa40fc996b7f27cc704149
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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