Stannous chloride dihydrate → 3-(2-isopropyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine

HRID 540562노트

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HRID 540562 반응식
[CH:1]([N:4]1[C:8]([C:9]2[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=2[O:18][CH3:19])=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2].O.O.Cl[Sn]Cl>C(O)C>[CH:1]([N:4]1[C:8]([C:9]2[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:10]=2[O:18][CH3:19])=[CH:7][CH:6]=[N:5]1)([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 61436Stannous chloride dihydrateHCID 231394531-isopropyl-5-(2-methoxy-5-nitro-phenyl)-1H-pyrazole

생성물 1

HCID 231395083-(2-isopropyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine수율 94%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
55 °C

실험 절차

To a solution of 1-isopropyl-5-(2-methoxy-5-nitro-phenyl)-1H-pyrazole, from Example 1.81, Step C (0.57 g, 2.18 mmol) in ethanol (5.0 mL), was added SnCl2.2H2O (1.97 g, 8.74 mmol) and the mixture was heated at 55° C. overnight. The ethanol was evaporated and the residue was taken in ethyl acetate (50 mL) and washed with 10% NaOH (10 mL). The organic layer was dried over MgSO4 and evaporated to yield a light yellow solid. The crude material was purified via Biotage silica chromatography (hexane/EtOAc, 3/1) to yield a pale yellow solid of 3-(2-isopropyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine (0.465 g, 94%). LCMS m/z (%)=232 M+H+ (100), 1H NMR (400 MHz, CDCl3) δ: 7.47 (s, 1H), 6.78 (d, J=8.08 Hz, 1H), 6.72 (dd, J1=8.01 Hz, J2=2.78 Hz, 1H), 6.54 (d, J=2.78 Hz, 1H), 6.25 (s, 1H), 4.14 (m, 1H), 3.63 (s, 3H), 1.4 (d, J=6.57 Hz, 3H), 1.23 (d, J=6.57 Hz, 3H).

후처리

  1. customThe ethanol was evaporated
  2. washwashed with 10% NaOH (10 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated
  5. customto yield a light yellow solid
  6. customThe crude material was purified via Biotage silica chromatography (hexane/EtOAc, 3/1)

출처 및 근거

ORD 기록
ord-b205626da02642269731d78259a59d54
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871797B2

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