Phenylboronic Acid → Ethyl 2-phenyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate

HRID 917298노트

반응식

HRID 917298 반응식
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9](Br)=[N:8][C:7]=1[C:12]([F:15])([F:14])[F:13])=[O:5])[CH3:2].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[F-].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)C>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:8][C:7]=1[C:12]([F:15])([F:14])[F:13])=[O:5])[CH3:2]

참가 물질

8

반응물 4

HCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 132827592-Bromo-4-trifluoromethyl-thiazole-5-carboxylic acid ethyl ester

생성물 1

HCID 1483699Ethyl 2-phenyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate수율 60%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

To a solution of thiazole III (2.0 g, 6.6 mmol) and the phenyl boronic acid (9.9 mmol) in THF (10 mL) was added potassium fluoride (1.15 g, 19.8 mmol), palladium (II) acetate (74 mg, 0.33 mmol), and 2-(di-t-butylphosphino)biphenyl (197 mg, 0.66 mmol). This mixture was stirred at 25° C. for 24 h. Diethyl ether (100 mL) was then added and the mixture was washed with 1 N aqueous NaOH (2×50 mL), saturated aqueous NaCl (1×50 mL), dried over MgSO4 and concentrated in vacuo to give an off-white solid. Purification by flash chromatography (silica, 0-2.5% ethyl acetate/hexane) gave the product, generally in 60-90% yield.

후처리

  1. washthe mixture was washed with 1 N aqueous NaOH (2×50 mL), saturated aqueous NaCl (1×50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customto give an off-white solid
  5. customPurification by flash chromatography (silica, 0-2.5% ethyl acetate/hexane)
  6. customgave the product

출처 및 근거

ORD 기록
ord-c71c4c60496a41b38418b116bdafcbe5
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07273866B2

반응 노트

불러오는 중…