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

HRID 1177523ノート

反応式

HRID 1177523 の反応式
[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

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
55 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fdebf256a1dc470082dc3b65a6c190a4
出典データセット
uspto-grants-2010_11
特許番号
US07842685B2

反応ノート

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