Pyridine → 1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-3-methyl-4-[(phenylmethyl)oxy]-1H-indazole

HRID 2423085ノート

反応式

HRID 2423085 の反応式
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH:4][N:3]=1.[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][C:28]=1[F:36])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:36][C:28]1[CH:29]=[C:30]([N:4]2[C:5]3[C:10](=[C:9]([O:11][CH2:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:8]=[CH:7][CH:6]=3)[C:2]([CH3:1])=[N:3]2)[CH:31]=[CH:32][C:27]=1[O:26][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 27377884-Benzyloxy-3-fluorophenylboronic AcidHCID 178434287HCID 178434287、化合物

生成物 1

HCID 592729801-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-3-methyl-4-[(phenylmethyl)oxy]-1H-indazole収率 25.7%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 3-methyl-4-[(phenylmethyl)oxy]-1H-indazole (D30) (0.952 g, 4 mmol), 4-benzyloxy-3-fluorobenzeneboronic acid (1.97 g, 8.0 mmol), copper (II) acetate (1.09 g, 6.0 mmol), pyridine (0.647 mL, 8.0 mmol) and powdered 4A molecular sieves (4 g) in dichloromethane (25 mL) was stirred in an air atmosphere at room temperature. After 48 hrs, the mixture was filtered through Celite, concentrated, redissolved in ethyl acetate, refiltered and concentrated and then chromatographed (0-50% ethyl acetate in hexane and 0-40% diethyl ether in hexane). A white solid crystallised out from some fractions and this was collected by filtration to give the title compound (D31) (0.45 g).

後処理

  1. filtrationthe mixture was filtered through Celite
  2. concentrationconcentrated
  3. dissolutionredissolved in ethyl acetate
  4. concentrationrefiltered and concentrated
  5. customchromatographed (0-50% ethyl acetate in hexane and 0-40% diethyl ether in hexane)
  6. customA white solid crystallised out from some fractions
  7. filtrationthis was collected by filtration

出典と根拠

ORDレコード
ord-79a1df85ff0b494093493feb9a88dd46
出典データセット
uspto-grants-2011_06
特許番号
US07960563B2

反応ノート

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