Pyrazole → 2-Methoxy-4-(1H-pyrazol-1-yl)aniline

HRID 32797

반응식

HRID 32797 반응식
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[CH:3]=1.[NH:11]1[CH:15]=[CH:14][CH:13]=[N:12]1.C([O-])([O-])=O.[K+].[K+].CN[C@H]1[C@H](NC)CCCC1.[Na+].[Cl-]>CN1C(=O)CCC1.[Cu]I.CCOC(C)=O>[CH3:10][O:9][C:4]1[CH:3]=[C:2]([N:11]2[CH:15]=[CH:14][CH:13]=[N:12]2)[CH:8]=[CH:7][C:5]=1[NH2:6]

참가 물질

9

반응물 5

HCID 1048PyrazoleHCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 4592574-Bromo-2-methoxyanilineHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

생성물 1

HCID 597943592-Methoxy-4-(1H-pyrazol-1-yl)aniline수율 90%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
150 °C

실험 절차

To a solution of 4-bromo-2-(methyloxy)aniline (400 mg, 1.979 mmol) in anh. NMP (4 mL), at r.t., under N2, were added pyrazole (269 mg, 2 eq), K2CO3 (819 mg, 3 eq), CuI (377 mg, 1 eq) and (1R,2R)-diaminomethylcyclohexane (281 mg, 1 eq). The reaction mixture was stirred at 150° C. for 3 hr. It was cooled down to r.t. and poured into EtOAc/sat.aq. NaCl. The phases were separated and the organic layer was washed with sat.aq. NH4Cl (20 mL) and sat.aq. NaCl (20 mL). The combined aqueous layers were extracted back with EtOAc (20 mL) and the combined organic extracts were dried over anh. Na2SO4. The solids were filtered and the solvent evaporated. The crude product was purified by flash chromatography (silica gel, cHex/EtOAc 7:3) to give the title compound as a brown oil (336 mg, 90%)

후처리

  1. temperatureIt was cooled down to r.t.
  2. customThe phases were separated
  3. washthe organic layer was washed with sat.aq
  4. extractionThe combined aqueous layers were extracted back with EtOAc (20 mL)
  5. dry with materialthe combined organic extracts were dried over anh. Na2SO4
  6. filtrationThe solids were filtered
  7. customthe solvent evaporated
  8. customThe crude product was purified by flash chromatography (silica gel, cHex/EtOAc 7:3)

출처 및 근거

ORD 기록
ord-9dae480e5d5e4f97b07f3895141283dc
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427630B2

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