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

HRID 2261746노트

반응식

HRID 2261746 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-255dbde049e6458ab97f759eac6ffc5f
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846960B2

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