Potassium Acetate → (2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)furo[2,3-b]pyridin-5-yl)boronic acid

HRID 595687

반응식

HRID 595687 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:23][C:11]3=[N:12][C:13]([N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])=[C:14](I)[CH:15]=[C:10]3[C:9]=2[C:24]([NH:26][CH3:27])=[O:25])=[CH:4][CH:3]=1.[B:28]([OH:33])([OH:32])B(O)O.CC([O-])=O.[K+]>CCO.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:23][C:11]3=[N:12][C:13]([N:17]([CH3:22])[S:18]([CH3:21])(=[O:20])=[O:19])=[C:14]([B:28]([OH:33])[OH:32])[CH:15]=[C:10]3[C:9]=2[C:24](=[O:25])[NH:26][CH3:27])=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 517044Potassium AcetateHCID 10986154Diboron tetrahydroxideHCID 545750872-(4-fluorophenyl)-5-iodo-N-methyl-6-(N-methylmethylsulfonamido)furo[2,3-b]pyridine-3-carboxamide

생성물 1

HCID 90332448(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)furo[2,3-b]pyridin-5-yl)boronic acid수율 197.8%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

To a degassed solution of 2-(4-fluorophenyl)-5-iodo-N-methyl-6-(N-methylmethylsulfonamido)furo[2,3-b]pyridine-3-carboxamide (prepared according to International Patent Application Publication No. WO2011131709, 3.0 g, 6 mmol), hypodiboric acid (1.08 g, 1.2 mmol) and KOAc (1.8 g, 1.8 mmol) in EtOH (60 mL) was added Pd(OAc)2 (50 mg) and Ad2n-BuP (50 mg) under nitrogen atmosphere. The reaction mixture was stirred at 80° C. for 5 h, concentrated in vacuo to remove EtOH. The residue was purified by column chromatography (EA:DCM=1:1˜DCM:MeOH=5:1) to afford the desired product of (2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)furo[2,3-b]pyridin-5-yl)boronic acid (1 g, yield: 40%). 1H-NMR (DMSO-d6, 400 MHz) δ 8.53 (d, J=4.4 Hz, 1H), 8.24 (s, 1H), 8.00˜8.04 (m, 3H), 7.40 (t, J=8.8 Hz, 2H), 4.08 (br s, 1H), 3.17 (s, 3H), 3.06 (s, 3H), 2.85 (d, J=4.8 Hz, 3H). MS (M+H)+: 422.

후처리

  1. concentrationconcentrated in vacuo
  2. customto remove EtOH
  3. customThe residue was purified by column chromatography (EA:DCM=1:1˜DCM:MeOH=5:1)

출처 및 근거

ORD 기록
ord-b72dd425d6c34f319586b2e04c3950bb
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243002B2

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