Toluene → 4-[(2-{[4-(1,3-Thiazol-2-yl)phenyl]oxy}ethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

HRID 1173430노트

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HRID 1173430 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][N:18]([CH2:31][C:32]([F:35])([F:34])[F:33])[C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=3)=[CH:11][CH:10]=2)O1.Br[C:38]1[S:39][CH:40]=[CH:41][N:42]=1.C([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1>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.O.CCO>[S:39]1[CH:40]=[CH:41][N:42]=[C:38]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][N:18]([CH2:31][C:32]([F:33])([F:34])[F:35])[C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[C:21]([C:27]([F:30])([F:28])[F:29])[CH:20]=2)=[CH:11][CH:10]=1

참가 물질

8

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 764302-BromothiazoleHCID 866237354-[(2-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}ethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

생성물 1

HCID 117197674-[(2-{[4-(1,3-Thiazol-2-yl)phenyl]oxy}ethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile수율 6.6%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매

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온도
80 °C

실험 절차

A mixture of 4-[(2-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}ethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.100 g, 0.19 mmol; step A above), 2-bromothiazole (0.020 mL, 0.21 mmol), Pd(PPh3)4 (0.011 g, 0.010 mmol), Na2CO3 (0.106 g, 1.00 mmol), toluene (1 mL), EtOH (0.50 mL) and H2O (0.5 mL) was sparged with N2 for 10 min and then heated at 80° C. in a sealed vial for 72 h. The mixture was cooled, poured into water, and extracted with EtOAc (×3). Combined organics were washed (H2O, brine), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.0059 g of the title compound as a yellow film: MS (ESI) m/z 472 (M+1).

후처리

  1. customwas sparged with N2 for 10 min
  2. temperatureThe mixture was cooled
  3. additionpoured into water
  4. extractionextracted with EtOAc (×3)
  5. washCombined organics were washed (H2O, brine)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-dbe2e545dd41424aa8fbb72b6e5d56a1
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834063B2

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