1,2-Dichloroethane → 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-methylpyridin

HRID 1789825ノート

反応式

HRID 1789825 の反応式
Br[C:2]1[CH:3]=[C:4]([CH3:23])[C:5]([N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[N:6][CH:7]=1.[C:24]([Si:28](C)(C)OC[Sn](CCCC)(CCCC)CCCC)([CH3:27])([CH3:26])[CH3:25].C([O:48][CH2:49][CH3:50])C.[F-].[K+].Cl[CH2:54]CCl>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:12]([O:11][C:9]([N:8]([C:5]1[C:4]([CH3:23])=[CH:3][C:2]([C:49]([CH3:50])([CH3:54])[O:48][SiH2:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:7][N:6]=1)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:10])([CH3:15])([CH3:14])[CH3:13]

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 3283Diethyl EtherHCID 522689Potassium FluorideHCID 14270862Tert-butyl-dimethyl-(tributylstannylmethoxy)silaneHCID 220360402-(N,N-BisBOC-amino)-5-bromo-3-methylpyridine

生成物 1

HCID 1317258272-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-methylpyridin収率 59%

試薬・触媒・溶媒 1

HCID 178418476HCID 178418476、化合物触媒

反応条件

温度
0 °C

実験手順

A solution of 5-bromo-2-[N,N-bis(tert-butoxycarbonyl)amino]-3-methyl-pyridin (26.0 g, 67.1 mmol), tert-butyl-dimethyl-tributylstannanylmethoxy-silane (47.6 g, 109 mmol), and bis(triphenylphosphine)palladium(II) dichloride (0.90 g, 1.42 mmol) in 1,2-dichloroethane (80 mL) was stirred at 90° C. for two days. The mixture was cooled to 0° C. and diethyl ether (200 mL) was added followed by saturated aqueous potassium fluoride (40 mL). The mixture was stirred vigourously for 30 min and filtered. The organic phase was washed with water, dried and concentrated under reduced pressure. Flash chromatography (hexane/EtOAc, 100:0→95:5) gave 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-methylpyridin (18.0 g, 59%).

後処理

  1. filtrationfiltered
  2. washThe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-36d991e903c24644903420e72332da4d
出典データセット
uspto-grants-2006_07
特許番号
US07071175B1

反応ノート

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