Ethanol → Methyl [3,5-bis(trifluoromethyl)benzyl][2-isoquinolin-4-yl-5-(trifluoromethyl)benzyl]carbamate

HRID 217527

반응식

HRID 217527 반응식
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1I)[C:8](=[O:11])[O:9][CH3:10].CCO.[CH:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:39](B(O)O)=[CH:38][N:37]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[C:39]1[C:40]2[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:36]=[N:37][CH:38]=1)[C:8](=[O:11])[O:9][CH3:10]

참가 물질

6

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 3761204Isoquinoline-4-boronic acidHCID 59343876Methyl [3,5-bis(trifluoromethyl)benzyl](2-iodo-5-trifluoromethyl-benzyl)carbamate

생성물 1

HCID 11563310Methyl [3,5-bis(trifluoromethyl)benzyl][2-isoquinolin-4-yl-5-(trifluoromethyl)benzyl]carbamate

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
97.5 °C

실험 절차

To a solution of methyl [3,5-bis(trifluoromethyl)benzyl](2-iodo-5-trifluoromethyl-benzyl)carbamate (41 mg, 0.070 mmol) (Example 5) in 3:2 EtOH:toluene, 4-isoquinolineboronic acid (18.2 mg, 0.105 mmol) and 2.5 M sodium carbonate (0.175 mmol) were added. The solution was degassed, followed by the addition of a catalytic amount of tetrakis(triphenylphosphine)palladium. The solution was stirred at 95-100° C. until completion of the reaction. Upon cooling, the solvent was removed in vacuo. The desired product was obtained by preparative thin layer chromatography using 25% acetone/hexane. 1H NMR (CDCl3, 500 MHz) δ 9.36 (s, 1H), 8.38 (s, 1H), 8.10-8.13 (m, 1H), 7.68-7.80 (m, 4H), 7.26-7.64 (m, 5H), 4.22-4.48 (m, 4H), 3.64-3.78 (m, 3H). LC-MS (M+1) 587.2 (3.48 min).

후처리

  1. customThe solution was degassed
  2. additionfollowed by the addition of a catalytic amount of tetrakis(triphenylphosphine)palladium
  3. temperatureUpon cooling
  4. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-14ce06d31f2c4c2db7a2fe467f7dd5af
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193365B2

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