Bromine → HCID 90413739, 화합물

HRID 1746074노트

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HRID 1746074 반응식
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[C:17]3[O:16][C:15]([F:19])([F:18])[O:14][C:13]=3[C:12]([Si](C)(C)C)=[CH:11][CH:10]=2)[N:5]=[C:4]([C:24]([O:26][CH3:27])=[O:25])[C:3]=1[Cl:28].[Br:29]Br.OS([O-])=O.[Na+]>ClCCCl>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[C:17]3[O:16][C:15]([F:19])([F:18])[O:14][C:13]=3[C:12]([Br:29])=[CH:11][CH:10]=2)[N:5]=[C:4]([C:24]([O:26][CH3:27])=[O:25])[C:3]=1[Cl:28]

참가 물질

5

반응물 3

HCID 24408BromineHCID 23665763Sodium BisulfiteHCID 90413465HCID 90413465, 화합물

생성물 1

HCID 90413739HCID 90413739, 화합물수율 92%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
22.5 °C

실험 절차

Methyl 4-amino-3-chloro-6-(2,2-difluoro-7-(trimethylsilyl)benzo[d][1,3]dioxol-4-yl)-5-fluoropicolinate (400 mg, 0.92 mmol) was stirred in 1,2-dichloroethane (5 mL), treated with bromine (1.0 g, 6.5 mmol) and stirred at 20-25° C. for 4 h. The solution was stirred with 10% NaHSO3 solution (30 mL) and extracted with ethyl acetate (35 mL). The organic phase was washed with saturated NaCl (5 mL), dried (Na2SO4) and evaporated to give the title compound as a white solid (370 mg, 92%): mp 168-170° C.; 1H NMR (400 MHz, CDCl3) δ 7.35 (m, 1H), 5.02 (s, 1H), 3.99 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −49.23, −137.58; ESIMS m/z 439 ([M+H]+), 437 ([M−H]−).

후처리

  1. extractionextracted with ethyl acetate (35 mL)
  2. washThe organic phase was washed with saturated NaCl (5 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated

출처 및 근거

ORD 기록
ord-4b3d086b8a3a423794a13cf074ac2e0a
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09149038B2

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