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

HRID 573594노트

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HRID 573594 반응식
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[CH:3]=1.O(C([N:35]1[CH:39]=[C:38](B(O)O)[CH:37]=[N:36]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:38]4[CH:39]=[N:35][NH:36][CH:37]=4)=[CH:3][C:4]=23)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=1

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 441186751-tert-Butoxycarbonyl-1H-pyrazole-4-boronic acidHCID 68323811Ethyl 2-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methylthieno[2,3-b]pyridine-5-carboxylate

생성물 1

HCID 68380155Ethyl 4-{[(3-chlorophenyl)sulfonyl]amino}-6-methyl-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridine-5-carboxylate

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

Alternatively, a mixture of ethyl 2-bromo-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methylthieno[2,3-b]pyridine-5-carboxylate (Description 72) (6.91 g, 14.11 mmol), 1-tert-butoxylcarbonyl-1H-pyrazole-4-boronic acid, pinacol ester (6.22 g, 21.16 mmol), tetrakis(triphenylphosphine)palladium(0) (0.408 g, 0.353 mmol) and potassium carbonate (5.85 g, 42.3 mmol) in 1,4-dioxane (50 mL), DMF (25 mL) and water (12.5 mL) was heated at 100° C. overnight (ca. 20 h). After cooling to RT, the reaction mixture was filtered through celite and the filtrate was concentrated. The residue was purified by chromatography on silica, eluting with a gradient of 0-100% ethyl acetate/DCM. The resulting material was then passed through an SCX cartridge, eluting with MeOH (150 mL) followed by 2M NH3 in MeOH (250 mL) and the basic methanolic fractions concentrated, to give the title compound (6.276 g).

후처리

  1. temperatureAfter cooling to RT
  2. filtrationthe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by chromatography on silica
  5. washeluting with a gradient of 0-100% ethyl acetate/DCM
  6. washeluting with MeOH (150 mL)
  7. concentrationthe basic methanolic fractions concentrated

출처 및 근거

ORD 기록
ord-1b1141c3f2b142ffb276ea10c5f44a0f
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029545B2

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