Cesium carbonate → 2-[4-[(1-Methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazole

HRID 1942638노트

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HRID 1942638 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([CH3:18])[CH3:17])=[C:11]([C:19]([F:22])([F:21])[F:20])[CH:10]=2)O1.Br[C:25]1[S:26][CH:27]=[CH:28][N:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:18][CH:16]([O:15][C:12]1[CH:13]=[CH:14][C:9]([C:25]2[S:26][CH:27]=[CH:28][N:29]=2)=[CH:10][C:11]=1[C:19]([F:20])([F:21])[F:22])[CH3:17]

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 764302-BromothiazoleHCID 58494057HCID 58494057, 화합물

생성물 1

HCID 669822262-[4-[(1-Methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazole수율 52.4%

시약·촉매·용매 3

HCID 178418807HCID 178418807, 화합물촉매HCID 962Water용매HCID 6342Acetonitrile용매

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온도
120 °C

실험 절차

To a solution of 4,4,5,5-tetramethyl-2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3,2-dioxaborolane (D42) (160 mg), 2-bromo-1,3-thiazole (119 mg) and cesium carbonate (237 mg) in acetonitrile (15 mL) and water (3.75 mL) stirred under nitrogen at room temperature was added PdCl2(dppf)-CH2Cl2 adduct (39.6 mg) in one charge. The reaction vessel was sealed and heated under microwave at 120° C. for 1 h. After cooling the reaction, the reaction mixture was filtered and the filtrate was partitioned between ethyl acetate (150 mL) and saturated brine (50 mL). The organic phase was dried over sodium sulphate and evaporated in vacuo. The crude product was purified by column chromatography to give 2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazole (D66) (73 mg). MS (ES): C13H12F3NOS requires 287. found 288.1 (M+H+).

후처리

  1. additioncharge
  2. customThe reaction vessel was sealed
  3. temperatureAfter cooling
  4. customthe reaction
  5. filtrationthe reaction mixture was filtered
  6. customthe filtrate was partitioned between ethyl acetate (150 mL) and saturated brine (50 mL)
  7. dry with materialThe organic phase was dried over sodium sulphate
  8. customevaporated in vacuo
  9. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-1f070925888b4a18a0544574ccb23e57
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389508B2

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