Water → Ethyl 7-(benzyloxy)-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylate

HRID 1486239Notes

Reaction equation

HRID 1486239 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[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:30]([O:35][CH2:36][CH3:37])(=[O:34])[C:31]#[C:32][CH3:33].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:23]([O:22][C:16]1[N:15]2[N:14]=[C:32]([CH3:33])[C:31]([C:30]([O:35][CH2:36][CH3:37])=[O:34])=[C:20]2[CH:19]=[C:18]([CH3:21])[CH:17]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 78043Ethyl 2-butynoateHCID 1178578501-Amino-2-(benzyloxy)-4-methylpyridinium 2,4,6-trimethylbenzenesulphonate

Product 1

HCID 117859771Ethyl 7-(benzyloxy)-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylateYield 33.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

11.7 g (28.2 mmol, 1.0 eq.) of 1-amino-2-(benzyloxy)-4-methylpyridinium 2,4,6-trimethylbenzenesulphonate from Example 6A were dissolved in 280 ml of DMF, and 6.6 ml (56 mmol, 2.0 eq.) of ethyl but-2-ynoate [CAS No: 4341-76-8] were added. 7.8 g (56 mmol, 2.0 eq.) of potassium carbonate were added and the mixture was stirred at RT for 1 h. Subsequently, 3.9 g (28 mmol, 1 eq.) of potassium carbonate were added and the mixture was stirred at RT for a further 16 h. Then the mixture was poured onto 540 ml of water and stirred briefly, and the precipitated solids were filtered off, washed with 220 ml of water and dried. 3.1 g of the title compound were obtained (34% of theory; 87% purity).

Workup

  1. stirringthe mixture was stirred at RT for a further 16 h
  2. stirringstirred briefly
  3. filtrationthe precipitated solids were filtered off
  4. washwashed with 220 ml of water
  5. customdried

Sources & evidence

ORD record
ord-6ecd5aa0f73345f3a5d3dcb8808457e9
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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