Water → 2-methyl-4-(1H-pyrazol-1-yl)aniline

HRID 32795

反応式

HRID 32795 の反応式
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[C:6]([O-])([O-])=O.[K+].[K+].CN[C@H:14]1[C@H:19]([NH:20]C)[CH2:18][CH2:17][CH2:16][CH2:15]1.O>CN1C(=O)CCC1.[Cu]I.CCOC(C)=O>[CH3:6][C:14]1[CH:15]=[C:16]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)[CH:17]=[CH:18][C:19]=1[NH2:20]

参加物

8

反応物 4

HCID 962WaterHCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamine

生成物 1

HCID 144502612-methyl-4-(1H-pyrazol-1-yl)aniline収率 70.3%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

A solution of intermediate 82 (200 mg, 0.7 mmol), 1H-pyrazole (95 mg, 2 eq), CuI (133 mg, 1 eq), K2CO3 (290 mg, 2.1 eq) and (1R,2R)-diaminomethylcyclohexane (100 mg, 1 eq) in anh. NMP (1 mL), under N2, was heated at 150° C. for 6 hr. It was cooled down to r.t. and poured into water. EtOAc was added and the phases were separated. The aqueous layer was further extracted with EtOAc (2×10 mL). The combined organic extracts were dried over anh. Na2SO4, the solids were filtered and the solvent evaporated. The residue was purified by flash-chromatography (silica gel, cHex/EtOAc 8:2) to give the title compound as a white solid (85.6 mg, 70%).

後処理

  1. customthe phases were separated
  2. extractionThe aqueous layer was further extracted with EtOAc (2×10 mL)
  3. dry with materialThe combined organic extracts were dried over anh. Na2SO4
  4. filtrationthe solids were filtered
  5. customthe solvent evaporated
  6. customThe residue was purified by flash-chromatography (silica gel, cHex/EtOAc 8:2)

出典と根拠

ORDレコード
ord-2f001b2f271244129c6d25a97321b00c
出典データセット
uspto-grants-2008_09
特許番号
US07427630B2

関連ノート

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