Potassium Carbonate → Ethyl 4-[(4-fluorobenzenesulfonyl)methylamino]-1,3-dimethyl-1h-pyrazolo[3,4-b] pyridine-5-carboxylate

HRID 496596

Reaction equation

Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]2[N:13]([CH3:17])[N:14]=[C:15]([CH3:16])[C:3]=12.CN[S:20]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)(=[O:22])=[O:21].C([O-])([O-])=O.[K+].[K+].[CH3:36][N:37]1CCCC1=O>C1OCCOCCOCCOCCOCCOC1>[F:29][C:26]1[CH:25]=[CH:24][C:23]([S:20]([CH2:36][NH:37][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]3[N:13]([CH3:17])[N:14]=[C:15]([CH3:16])[C:3]=23)(=[O:21])=[O:22])=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2.53 g (0.01 mol) of ethyl 4-chloro-1,3-dimethyl-1H pyrazolo[3,4-b]pyridine-5-carboxylate, 1.89 g (0.01 mol) of N-methyl-4-fluorobenzenesulfonamide, 6.91 g (0.05 mol) of anhydrous K2CO3, 0.143 g of 18-crown-6 and 70 ml of anhydrous 1-methyl-2-pyrrolidinone was stirred and heated at 100° C. for 17 hours. The solvent was removed under vacuum and water added to the residue. The mixture was extracted with CH2Cl2, and the extract washed with H2O, brine and dried (Na2SO4). The solution was filtered through a pad of hydrous magnesium silicate and the filtrate concentrated to dryness under vacuum to give 4.98 g of an oil. This oil was chromatographed on a silica gel column with ethyl acetate-hexane(2:3) as solvent to give 3.15 g of solid, mp 107-109° C.

Workup

customThe solvent was removed under vacuum and water
additionadded to the residue
extractionThe mixture was extracted with CH2Cl2
washthe extract washed with H2O, brine
dry with materialdried (Na2SO4)
filtrationThe solution was filtered through a pad of hydrous magnesium silicate
concentrationthe filtrate concentrated to dryness under vacuum

Sources & evidence

ORD record: ord-4b82875573834294837352ec2141a354
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06946473B2

Linked notes

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