Water → 2-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazole

HRID 1942641노트

반응식

HRID 1942641 반응식
[Cl:1][C:2]1[CH:3]=[C:4](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].Br[C:22]1[S:23][CH:24]=[CH:25][N:26]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>COCCOC.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>[Cl:1][C:2]1[CH:3]=[C:4]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

참가 물질

7

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 764302-BromothiazoleHCID 584941012-(3-Chloro-4-isopropoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 584941402-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazole수율 58.4%

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a suspension of 2-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (D69) (3 g), 2-bromo-1,3-thiazole (1.659 g) and Cs2CO3 (3.95 g) in 1,2-dimethoxyethane (DME) (40 mL)/water (10 mL) stirred under nitrogen at room temperature was added PdCl2(dppf)-CH2Cl2 adduct (661 mg) in one charge. The reaction vessel was sealed and heated under microwave at 120° C. for 2 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-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazole (D70) (1.5 g). MS (ES): C12H12ClNOS requires 253. found 254.1 (M+H+).

후처리

  1. additioncharge
  2. customThe reaction vessel was sealed
  3. temperatureheated under microwave at 120° C. for 2 h
  4. temperatureAfter cooling
  5. customthe reaction
  6. filtrationthe reaction mixture was filtered
  7. customthe filtrate was partitioned between ethyl acetate (150 mL) and saturated brine (50 mL)
  8. dry with materialThe organic phase was dried over sodium sulphate
  9. customevaporated in vacuo
  10. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-efb2454fa1a8478ab4cfe6942cae6185
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389508B2

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