Potassium Carbonate → Ethyl 4-{[(3-chlorophenyl)sulfonyl]amino}-3,6-dimethyl-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridine-5-carboxylate

HRID 573583Notes

Reaction equation

HRID 573583 reaction equation
Br[C:2]1[S:27][C:5]2=[N:6][C:7]([CH3:26])=[C:8]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:9]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)(=[O:13])=[O:12])=[C:4]2[C:3]=1[CH3:28].O(C([N:36]1[CH:40]=[C:39](B(O)O)[CH:38]=[N:37]1)=O)C(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:20][C:16]1[CH:15]=[C:14]([S:11]([NH:10][C:9]2[C:8]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:7]([CH3:26])[N:6]=[C:5]3[S:27][C:2]([C:39]4[CH:40]=[N:36][NH:37][CH:38]=4)=[C:3]([CH3:28])[C:4]=23)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 441186751-tert-Butoxycarbonyl-1H-pyrazole-4-boronic acidHCID 68324133Ethyl 2-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylate

Product 1

HCID 68324136Ethyl 4-{[(3-chlorophenyl)sulfonyl]amino}-3,6-dimethyl-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridine-5-carboxylate

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 2-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylate (Description 63) (350 mg, 0.695 mmol), 1-tert-butoxylcarbonyl-1H-pyrazole-4-boronic acid, pinacol ester (221 mg, 0.751 mmol), tetrakis(triphenylphosphine)palladium(0) (40.1 mg, 0.035 mmol) and potassium carbonate (288 mg, 2.084 mmol) in 1,4-dioxane (1.5 mL), DMF (1.5 mL) and water (0.5 mL) was heated at 100° C. overnight (ca. 16 h). The reaction mixture was cooled to RT, filtered through celite and the filtrate was concentrated. The residue was purified by normal phase chromatography, eluting with a gradient of 0-100% ethyl acetate in cyclohexane, to give the title compound (150 mg). LCMS (A) m/z: 491 [M+1]+, Rt 1.20 min (acidic).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered through celite
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by normal phase chromatography
  5. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-689c82437a944309b1daa7b7260cce35
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

Loading…