Tributylphosphine → 4-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenylamine

HRID 2261746ノート

反応式

HRID 2261746 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][OH:15])=[C:12]([CH:16]([CH3:18])[CH3:17])[CH:11]=[N:10]1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23](O)=[CH:22][C:21]=1[CH3:27].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[N:9]1[C:13]([CH2:14][O:15][C:23]2[CH:24]=[CH:25][C:20]([NH2:19])=[C:21]([CH3:27])[CH:22]=2)=[C:12]([CH:16]([CH3:18])[CH3:17])[CH:11]=[N:10]1

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 178194-Amino-m-cresolHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 57443256(1-(2,6-dichlorophenyl)-4-isopropyl-1H-pyrazol-5-yl)methanol

生成物 1

HCID 675278794-[2-(2,6-Dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-ylmethoxy]-2-methyl-phenylamine収率 56%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

To a 0° C. solution of [2-(2,6-dichloro-phenyl)-4-isopropyl-2H-pyrazol-3-yl]-methanol (3.0 g, 10.6 mmol), 4-amino-3-methyl-phenol (2.0 g, 15.8 mmol), and tri-n-butylphosphine (3.2 g, 15.8 mmol) in toluene (30 mL) is added a solution of 1,1′-(Azodicarbonyl)-dipiperidine (4.0 g, 15.8 mmol) in toluene (40 mL). The reaction mixture is allowed to warm to room temperature and is stirred for 3.0 h. The reaction mixture is partitioned between EtOAc (50 mL) and water (60 mL). The organic layer is washed with brine (60 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography (EtOAc/Hexane) to afford the title compound as a solid (2.3 g, 56%). LC-ES/MS m/e 390.0 (M+1).

後処理

  1. customThe reaction mixture is partitioned between EtOAc (50 mL) and water (60 mL)
  2. washThe organic layer is washed with brine (60 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to a residue
  6. customThe residue is purified by flash chromatography (EtOAc/Hexane)

出典と根拠

ORDレコード
ord-255dbde049e6458ab97f759eac6ffc5f
出典データセット
uspto-grants-2010_12
特許番号
US07846960B2

反応ノート

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