Sodium Carbonate → HCID 56980562, 화합물

HRID 379991

반응식

HRID 379991 반응식
[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

참가 물질

7

반응물 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

생성물 1

HCID 56980562HCID 56980562, 화합물수율 35.9%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2854a5807d2948f79424758aee06ed73
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300352B1

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