Ammonium Chloride → Benzyl 2-(7-bromo-6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamate

HRID 915745

반응식

HRID 915745 반응식
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH2:11][CH:12]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:13])=[CH:4][CH:3]=1.[Br:25]N1C(=O)CCC1=O.[Cl-].[NH4+]>ClCCl.O1CCCC1>[Br:25][C:10]1[C:2]([OH:1])=[CH:3][CH:4]=[C:5]2[C:9]=1[N:8]([CH2:11][CH:12]([NH:14][C:15](=[O:24])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:13])[N:7]=[CH:6]2

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 67184N-bromobutanimideHCID 136338685benzyl 2-(6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamate

생성물 1

HCID 136338690Benzyl 2-(7-bromo-6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of benzyl 2-(6-hydroxy-1H-indazol-1-yl)-1-methylethylcarbamate (0.90 g, 2.98 mmol) in dichloromethane (10 mL) and tetrahydrofuran (5 mL) was added N-bromosuccinimide (0.59 g, 3.38 mmol) at room temperature. After 16 h, a saturated aqueous solution of ammonium chloride (25 mL) was added and this mixture was extracted with ethyl acetate (3×60 mL). The combined extracts were washed with brine (10 mL), dried (magnesium sulfate), and evaporated. The residue was purified by chromatography (silica, 30% to 50% ethyl acetate in hexane) to give (1.1 g, 91%): 1H NMR (CDCl3) δ 7.86 (1H, d, J=8.8 z), 7.80 (1H, s), 7.37 (6H, m), 6.18 (1H, brs), 5.24 (1H, brs), 4.95 (2H, s), 4.80 (2H, m), 4.34 (1H, m), 1.26 (3H, d, J=6.8 Hz); MS (ES) m/z 404, 406 (M+).

후처리

  1. extractionthis mixture was extracted with ethyl acetate (3×60 mL)
  2. washThe combined extracts were washed with brine (10 mL)
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated
  5. customThe residue was purified by chromatography (silica, 30% to 50% ethyl acetate in hexane)
  6. customto give (1.1 g, 91%)

출처 및 근거

ORD 기록
ord-3f41f0e706004e2f9b36398d2ee3a9e1
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07268131B2

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