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4-(Tributylstannyl)pyridazine → Tert-butyl 2-(3-methyl-4-(pyridazin-4-yl)phenyl)acetate

HRID 1036211
ノート
印刷プレビュー

反応式

HRID 1036211 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=1[CH3:16].C([Sn](CCCC)(CCCC)[C:22]1[CH:27]=[CH:26][N:25]=[N:24][CH:23]=1)CCC>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.CN(C=O)C>[CH3:16][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:6]=[CH:7][C:2]=1[C:22]1[CH:27]=[CH:26][N:25]=[N:24][CH:23]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 64097334-(Tributylstannyl)pyridazineHCID 58447742Tert-butyl 2-(4-bromo-3-methylphenyl)acetate

生成物 1

HCID 58447683Tert-butyl 2-(3-methyl-4-(pyridazin-4-yl)phenyl)acetate

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
118 °C

実験手順

A mixture of tert-butyl 2-(4-bromo-3-methylphenyl)acetate (855 mg, 3.00 mmol), 4-(tributylstannyl)pyridazine (1162 mg, 3.15 mmol), Pd(PPh3)4 (173 mg, 0.15 mmol) and DMF (10 ml) was stirred under argon atmosphere at 118° C. overnight. After cooled to room temperature, the mixture was concentrated by evaporation of DMF, redissolved in ethyl acetate (50 ml) and washed with water (50 ml×2). After dried over Na2SO4 and concentrated by evaporation, the mixture was subjected to silica gel column chromatography with ethyl acetate/hexanes (1:1) as eluent to give tert-butyl 2-(3-methyl-4-(pyridazin-4-yl)phenyl)acetate 134-2 as an oil.

後処理

  1. temperatureAfter cooled to room temperature
  2. concentrationthe mixture was concentrated by evaporation of DMF
  3. dissolutionredissolved in ethyl acetate (50 ml)
  4. washwashed with water (50 ml×2)
  5. dry with materialAfter dried over Na2SO4
  6. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-3bc0cf9adf534a84b1804729329f20b4
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546396B2

反応ノート

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