Sodium Carbonate → HCID 59127378、化合物

HRID 2246612ノート

反応式

HRID 2246612 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:6]=[CH:5]2.[CH:18]1([NH:21][C:22]([C:24]2[CH:25]=[C:26]([F:34])[C:27]([CH3:33])=[C:28](B(O)O)[CH:29]=2)=[O:23])[CH2:20][CH2:19]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:18]1([NH:21][C:22]([C:24]2[CH:25]=[C:26]([F:34])[C:27]([CH3:33])=[C:28]([C:2]3[CH:3]=[C:4]4[C:8](=[CH:9][CH:10]=3)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:6]=[CH:5]4)[CH:29]=2)=[O:23])[CH2:20][CH2:19]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 21914527(5-(Cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl)boronic acidHCID 228320255-Bromo-1H-indazole, N1-BOC protected2 回

生成物 1

HCID 59127378HCID 59127378、化合物収率 211.1%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of tert-butyl 5-bromo-1H-indazole-1-carboxylate (Intermediate 1, 1.07 g), {5-[(cyclopropylamino)carbonyl]-3-fluoro-2-methylphenyl}boronic acid (0.85 g), sodium carbonate (1.9 g) and tetrakis(triphenylphosphine)palladium(0) (0.42 g) in 1,2-dimethoxyethane (70 ml) was stirred at reflux under nitrogen for 20 h. The solvent was removed and the residue was partitioned between water (50 ml) and ethyl acetate (50 ml). The aqueous layer was re-extracted with ethyl acetate (3×30 ml) and the combined organic extracts were dried using a hydrophobic filter tube and concentrated under vacuum. The residue was purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (75:25 to 60:40) to give the title compound (3.1 g).

後処理

  1. temperatureat reflux under nitrogen for 20 h
  2. customThe solvent was removed
  3. customthe residue was partitioned between water (50 ml) and ethyl acetate (50 ml)
  4. extractionThe aqueous layer was re-extracted with ethyl acetate (3×30 ml)
  5. customthe combined organic extracts were dried
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography on silica eluting with cyclohexane:ethyl acetate (75:25 to 60:40)

出典と根拠

ORDレコード
ord-a3e918193024463c81fd82d719a78adb
出典データセット
uspto-grants-2010_03
特許番号
US07687532B2

反応ノート

読み込み中…