2-Fluoro-4-iodopyridine-3-carbaldehyde → 3-(4-iodo-1H-pyrazolo[3,4-b]pyridin-1-yl)benzenesulfonamide

HRID 1186789노트

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HRID 1186789 반응식
F[C:2]1[N:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[CH:4]=O.[NH:11]([C:13]1[CH:14]=[C:15]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1)[NH2:12]>CN1C(=O)CCC1>[I:10][C:6]1[CH:7]=[CH:8][N:9]=[C:2]2[N:11]([C:13]3[CH:14]=[C:15]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=3)[N:12]=[CH:4][C:3]=12

참가 물질

4

반응물 2

HCID 99923282-Fluoro-4-iodopyridine-3-carbaldehydeHCID 148372153-Hydrazinylbenzenesulfonamide

생성물 1

HCID 666648613-(4-iodo-1H-pyrazolo[3,4-b]pyridin-1-yl)benzenesulfonamide수율 25.4%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
185 °C

실험 절차

To a 45 mL pressure bottle was added 2-fluoro-4-iodonicotinaldehyde (1.05 g, 4.18 mmol), 3-hydrazinylbenzenesulfonamide (800 mg, 4.27 mmol), and anhydrous NMP (15 mL). The reaction mixture was flushed with argon, securely capped, and heated at 185° C. for 6.5 h. The reaction mixture was cooled to room temperature and slowly added to a rapidly stirred solution of diethyl ether (430 mL). The resulting solid material was filtered and the pale yellow Et2O filtrate was allowed to stand for 18 h at room temperature. The yellow crystals precipitated out and were collected by vacuum filtration to give 425 mg (16.42%) of the title compound as a yellow solid as a “dot” 2 NMP complex by proton NMR. LC/MS (Condition B): ret. T=3.2 min, (M+H)+ 400.83. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.56 (s, 2 H) 7.78-7.84 (m, 2 H) 7.89-7.92 (m, 1 H) 8.37-8.42 (m, 2 H) 8.57 (dt, J=4.81, 2.33 Hz, 1 H) 8.75 (s, 1 H). Second and third crops of yellow solid (300 mg, 11.7%; 246 mg, 9.4%) were identical to the first crop of material.

후처리

  1. customThe reaction mixture was flushed with argon
  2. customsecurely capped
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additionslowly added to a rapidly stirred solution of diethyl ether (430 mL)
  5. filtrationThe resulting solid material was filtered
  6. customThe yellow crystals precipitated out
  7. filtrationwere collected by vacuum filtration

출처 및 근거

ORD 기록
ord-abac8150514d463296a915c4ffecdeca
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673922B2

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