Pyridine → HCID 67427596, 화합물

HRID 1907803노트

반응식

HRID 1907803 반응식
[CH3:1][C:2]1([CH3:14])[CH2:12][C:5]2[S:6][C:7]([C:9]([OH:11])=O)=[CH:8][C:4]=2[C:3]1=[O:13].[F:15][C:16]1[CH:22]=[CH:21][C:20]([B:23]2[O:27][C:26]([CH3:29])([CH3:28])[C:25]([CH3:31])([CH3:30])[O:24]2)=[CH:19][C:17]=1[NH2:18].N1C=CC=CC=1>C(Cl)Cl>[F:15][C:16]1[CH:22]=[CH:21][C:20]([B:23]2[O:27][C:26]([CH3:28])([CH3:29])[C:25]([CH3:31])([CH3:30])[O:24]2)=[CH:19][C:17]=1[NH:18][C:9]([C:7]1[S:6][C:5]2[CH2:12][C:2]([CH3:1])([CH3:14])[C:3](=[O:13])[C:4]=2[CH:8]=1)=[O:11]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 467379902-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 58540128HCID 58540128, 화합물

생성물 1

HCID 67427596HCID 67427596, 화합물수율 45%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen and charged with 9 (270 mg, 1.29 mmol) and methylene chloride (3 mL). The solution Was cooled to 0° C., and 15 (172 mg, 1.29 mmol) was added dropwise. After this addition was complete, the reaction was warmed to room temperature and stirred for 2 h. 14 (305 mg, 1.29 mmol) was then added. After this addition, the reaction was cooled to 0° C., and anhydrous pyridine (306 mg, 3.87 mmol) was added. The cooling bath was removed, and the reaction mixture was stirred at room temperature for 16 h. After this time, the solvents were removed under reduced pressure, and the resulting residue was partitioned between water (10 mL) and methylene chloride (20 mL). The layers were separated, and the aqueous phase was extracted with methylene chloride (2×10 mL). The organic extracts were combined and dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography to afford 27 in 45% yield (235 mg) as a white solid: mp 88-89° C.; 1H NMR (500 MHz, CDCl3) δ 8.73 (d, J=8.5 Hz), 7.87 (s, 1H), 7.62 (s, 1H), 7.56 (t, 1H, J=6.5 Hz), 7.14 (dd, 1H, J=11.0, 8.5 Hz), 3.11 (s, 2H) 1.38 (s, 12H), 1.33 (s, 6H); MS (APCI+) m/z 430.3 (M+H).

후처리

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. additionAfter this addition
  4. temperaturethe reaction was warmed to room temperature
  5. additionAfter this addition
  6. temperaturethe reaction was cooled to 0° C.
  7. customThe cooling bath was removed
  8. stirringthe reaction mixture was stirred at room temperature for 16 h
  9. customAfter this time, the solvents were removed under reduced pressure
  10. customthe resulting residue was partitioned between water (10 mL) and methylene chloride (20 mL)
  11. customThe layers were separated
  12. extractionthe aqueous phase was extracted with methylene chloride (2×10 mL)
  13. dry with materialdried over sodium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated under reduced pressure
  16. customThe resulting residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-bcef8f3d05b8482da057374323222efb
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598174B2

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