Stannane → 4-(2,2-dimethylpropyl)-2-{1-[4-(5-fluoropyridin-2-yl)benzyl]vinyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

HRID 425430

反応式

HRID 425430 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.Br[C:10]1[CH:34]=[CH:33][C:13]([CH2:14][C:15]([C:17]2[N:18]([S:27]([N:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])[CH:19]=[C:20]([CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[N:21]=2)=[CH2:16])=[CH:12][CH:11]=1.[SnH4]>COCCOC.C(OCC)(=O)C.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>[CH3:24][C:23]([CH3:26])([CH3:25])[CH2:22][C:20]1[N:21]=[C:17]([C:15]([CH2:14][C:13]2[CH:12]=[CH:11][C:10]([C:2]3[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=3)=[CH:34][CH:33]=2)=[CH2:16])[N:18]([S:27]([N:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])[CH:19]=1

参加物

7

反応物 3

HCID 123161StannaneHCID 27831712-Bromo-5-fluoropyridineHCID 667056182-[1-(4-bromobenzyl)vinyl]-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

生成物 1

HCID 667058444-(2,2-dimethylpropyl)-2-{1-[4-(5-fluoropyridin-2-yl)benzyl]vinyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒2 回HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

Pd(PPh3)4 (196 mg) was added to a solution of 2-bromo-5-fluoropyridine in DME (10 mL) at ambient temperature. After heating at 90° C. overnight the reaction mixture was cooled. 2-[1-(4-bromobenzyl)vinyl]-4-(2,2-dimethylpropyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (110 mg) was added to the stannane solution followed by Pd(PPh3)4 (100 mg). After stirring at 95° C. overnight, the reaction mixture was cooled, diluted with ethyl acetate and washed with water. The organic phase was dried (sodium sulfate) and concentrated. Chromatography of the resulting crude product over silica eluting with 0-50% ethyl acetate/hexanes afforded 4-(2,2-dimethylpropyl)-2-{1-[4-(5-fluoropyridin-2-yl)benzyl]vinyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide.

後処理

  1. temperaturewas cooled
  2. temperaturethe reaction mixture was cooled
  3. washwashed with water
  4. dry with materialThe organic phase was dried (sodium sulfate)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-6057f7179c1c4696909845307f399c60
出典データセット
uspto-grants-2012_01
特許番号
US08106070B2

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