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

HRID 1177523Notes

Reaction equation

HRID 1177523 reaction equation
[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

Participants

8

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fdebf256a1dc470082dc3b65a6c190a4
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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