Sodium Carbonate → HCID 56980562、化合物

HRID 379991

反応式

HRID 379991 の反応式
[Si]([O:8][C@H:9]([CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[C@H:10]([CH3:21])[O:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.Cl.Br[C:32]1[CH:33]=[C:34]([CH2:38][CH2:39][N:40]([CH3:42])[CH3:41])[CH:35]=[CH:36][CH:37]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.[Pd]>[CH3:42][N:40]([CH3:41])[CH2:39][CH2:38][C:34]1[CH:33]=[C:32]([C:15]2[CH:14]=[CH:13][C:12]([O:11][C@@H:10]([CH3:21])[C@H:9]([OH:8])[CH2:22][CH2:23][C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[CH:17][CH:16]=2)[CH:37]=[CH:36][CH:35]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 18367547[2-(3-Bromophenyl)ethyl]dimethylamine hydrochlorideHCID 54020751(1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxy]benzeneboronic acid

生成物 1

HCID 56980562HCID 56980562、化合物収率 35.9%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

Prepared according to the method described in Example 12b) from (1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxy]benzeneboronic acid (0.2 g, Example 11), [2-(3-bromophenyl)ethyl]dimethylamine hydrochloride (0.21 g, Example 27a)), aqueous sodium carbonate (2M, 0.82 ml) and tertakistriphenylphosphine palladium (0) (0.1 g) in toluene (5 ml) and ethanol (2 ml). The reaction was heated at 100° C. for 4 hours. After cooling, the solution was concentrated under reduced pressure. Concentrated hydrochloric acid (1 ml) was added to a solution of the residue in methanol (5 ml) and stirred at room temperature for 2 hours. After work up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane to give the title compound as an oil (0.07 g).

後処理

  1. customPrepared
  2. temperatureAfter cooling
  3. concentrationthe solution was concentrated under reduced pressure
  4. additionConcentrated hydrochloric acid (1 ml) was added to a solution of the residue in methanol (5 ml)
  5. customAfter work up, the residue was purified by normal-phase HPLC
  6. washeluting with a gradient of 0-25% ethanol in dichloromethane

出典と根拠

ORDレコード
ord-2854a5807d2948f79424758aee06ed73
出典データセット
uspto-grants-2001_10
特許番号
US06300352B1

関連ノート

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