Cesium fluoride → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-cyclohexylvinyl)thiazolo[5,4-b]pyridine

HRID 1177523노트

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HRID 1177523 반응식
[F-].[Cs+].Br[C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[CH2:5].[O:12]1[CH2:17][CH2:16][CH2:15][O:14][CH:13]1[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[S:25][C:26]3[C:31]([N:32]=2)=[CH:30][CH:29]=[C:28]([Sn](C)(C)C)[N:27]=3)=[C:20]([F:37])[CH:19]=1>CN(C=O)C.CC(=O)OCC.[Cu]I.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:12]1[CH2:17][CH2:16][CH2:15][O:14][CH:13]1[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[S:25][C:26]3[C:31]([N:32]=2)=[CH:30][CH:29]=[C:28]([C:4]([CH:6]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)=[CH2:5])[N:27]=3)=[C:20]([F:37])[CH:19]=1

참가 물질

8

반응물 3

HCID 25953Cesium fluorideHCID 11805501(1-Bromovinyl)cyclohexaneHCID 591748322-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(trimethylstannyl)thiazolo[5,4-b]pyridine

생성물 1

HCID 671116042-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-cyclohexylvinyl)thiazolo[5,4-b]pyridine

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
55 °C

실험 절차

A mixture of copper(I) iodide (0.0159 g, 0.0835 mmol), cesium fluoride (0.380 g, 2.50 mmol), (1-bromovinyl)cyclohexane (0.947 g, 5.01 mmol), tetrakis(triphenylphosphine) palladium (0) (0.0965 g, 0.0835 mmol), and 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(trimethylstannyl)-thiazolo[5,4-b]pyridine (0.800 g, 1.67 mmol) in 7.5 mL DMF was heated at 55° C. for several hours. The reaction mixture was cooled, diluted with EA, and filtered through celite. The organic layer was washed with water, brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a solid, which was adsorbed onto silica gel and purified by silica gel chromatography, 0-40-100% EA/hexanes to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-cyclohexylvinyl)thiazolo[5,4-b]pyridine as an off white solid. MS (ESI) m/z: calculated: 424.2; Observed: 425.1 (M++1).

후처리

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through celite
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a solid, which
  8. custompurified by silica gel chromatography, 0-40-100% EA/hexanes

출처 및 근거

ORD 기록
ord-fdebf256a1dc470082dc3b65a6c190a4
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842685B2

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