Water → Methyl 7-[(2,6-difluorobenzyl)oxy]-5-methyl-2-propylpyrazolo[1,5-a]pyridine-3-carboxylate

HRID 1486279Notes

Reaction equation

HRID 1486279 reaction equation
CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:14][N+:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[O:22][CH2:23][C:24]1[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=1[F:31].[C:32]([O:39][CH3:40])(=[O:38])[C:33]#[C:34][CH2:35][CH2:36][CH3:37].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:30][C:29]1[CH:28]=[CH:27][CH:26]=[C:25]([F:31])[C:24]=1[CH2:23][O:22][C:16]1[N:15]2[N:14]=[C:34]([CH2:35][CH2:36][CH3:37])[C:33]([C:32]([O:39][CH3:40])=[O:38])=[C:20]2[CH:19]=[C:18]([CH3:21])[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 87860Methyl 2-hexynoateHCID 117857852HCID 117857852, compound

Product 1

HCID 117859671Methyl 7-[(2,6-difluorobenzyl)oxy]-5-methyl-2-propylpyrazolo[1,5-a]pyridine-3-carboxylateYield 44.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.50 g (1.01 mmol) of 1-amino-2-[(2,6-difluorobenzyl)oxy]-4-methylpyridinium 2,4,6-trimethylbenzenesulphonate from Example 2A were dissolved in 3.3 ml of DMF, and 229 mg (1.82 mmol) of methyl hex-2-ynoate were added. 251 mg (1.82 mmol) of potassium carbonate were added and the mixture was stirred at RT for 3 h. Subsequently, the mixture was poured onto 24 ml of water and stirred briefly, and the precipitated solids were filtered off, washed with water and dried. 169 mg of the title compound were obtained (42% of theory; 95% purity).

Workup

  1. stirringstirred briefly
  2. filtrationthe precipitated solids were filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-957dd9e38607423c83775c704510a467
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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