Water → ethyl 2-phenyl-5-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)thiazole-4-carboxylate

HRID 453300노트

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HRID 453300 반응식
Br[C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH2:18]([O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1)[C:19]#[CH:20].C(N(CC)CC)C.O>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:7]1([C:5]2[S:6][C:2]([C:20]#[C:19][CH2:18][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)=[C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:4]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 44558337Ethyl 5-bromo-2-phenylthiazole-4-carboxylate

생성물 1

HCID 67425248ethyl 2-phenyl-5-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)thiazole-4-carboxylate수율 89%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
100 °C

실험 절차

Nitrogen was bubbled through a solution of Ethyl 5-bromo-2-phenylthiazole-4-carboxylate (3.6 g, 11.5 mmol) and 2-(prop-2-ynyloxy)tetrahydro-2H-pyran (3.3 mL, 23.1 mmol) in THF (30 mL). Dichlorobis(triphenylphosphine)palladium (II) (405 mg, 0.6 mmol), copper (I) iodide (55 mg, 0.3 mmol), and triethylamine (TEA) (8 mL, 57.7 mmol) were added and the reaction mixture was heated at 100° C. for 30 min in a microwave reactor. The reaction mixture was poured into H2O and extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4), and concentrated. The crude product was purified by MPLC eluting with pentane/EtOAc (0-50% gradient) to give ethyl 2-phenyl-5-(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)thiazole-4-carboxylate (3.8 g, 88% yield).

후처리

  1. extractionextracted with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product was purified by MPLC
  6. washeluting with pentane/EtOAc (0-50% gradient)

출처 및 근거

ORD 기록
ord-b3aa220436fd47ccbc625742a319b98b
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492401B2

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