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

HRID 573588ノート

反応式

HRID 573588 の反応式
Br[C:2]1[S:26][C:5]2=[N:6][C:7]([CH3:25])=[C:8]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:9]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])=[C:4]2[CH:3]=1.O(C([N:34]1[CH:38]=[C:37](B(O)O)[CH:36]=[N:35]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>[CH3:25][C:7]1[N:6]=[C:5]2[S:26][C:2]([C:37]3[CH:38]=[N:34][NH:35][CH:36]=3)=[CH:3][C:4]2=[C:9]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:8]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 441186751-tert-Butoxycarbonyl-1H-pyrazole-4-boronic acidHCID 68324051Ethyl 2-bromo-6-methyl-4-[(phenylsulfonyl)amino]thieno[2,3-b]pyridine-5-carboxylate

生成物 1

HCID 68380512Ethyl 6-methyl-4-[(phenylsulfonyl)amino]-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridine-5-carboxylate

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

A mixture of ethyl 2-bromo-6-methyl-4-[(phenylsulfonyl)amino]thieno[2,3-b]pyridine-5-carboxylate (Description 67) (6.27 g, 13.77 mmol), 1-tert-butoxylcarbonyl-1H-pyrazole-4-boronic acid, pinacol ester (8.10 g, 27.5 mmol), tetrakis(triphenylphosphine)palladium(0) (0.796 g, 0.688 mmol) and potassium carbonate (5.71 g, 41.3 mmol) in 1,4-dioxane (40 mL), DMF (20 mL) and water (10 mL) was heated at 100° C. for ca. 3.5 h. After cooling to RT, the reaction mixture was filtered through celite and the filtrate was concentrated. The residue was purified via normal phase chromatography eluting with 0-100% ethyl acetate in DCM, to give the title compound (5.81 g). LCMS (A) m/z: 443 [M+1]+, Rt 1.05 min (acidic).

後処理

  1. temperatureAfter cooling to RT
  2. filtrationthe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified via normal phase chromatography
  5. washeluting with 0-100% ethyl acetate in DCM

出典と根拠

ORDレコード
ord-e182394b2310474690e8a252bf05e8b4
出典データセット
uspto-grants-2015_05
特許番号
US09029545B2

反応ノート

読み込み中…