Water → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclopent-3-enyl)thiazolo[5,4-b]pyridine

HRID 1177426Notes

Reaction equation

HRID 1177426 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([C:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([CH2:26]C=C)[CH2:23][CH:24]=[CH2:25])[N:16]=3)=[C:9]([F:35])[CH:8]=1.O>C(Cl)Cl.CC1C=C(C)C(N2[CH-]N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1CCC([PH+](C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[O:3]1[CH2:4][CH2:5][CH2:6][O:1][CH:2]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15]3[C:20]([N:21]=2)=[CH:19][CH:18]=[C:17]([C:22]2([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:23][CH:24]=[CH:25][CH2:26]2)[N:16]=3)=[C:9]([F:35])[CH:8]=1

Participants

5

Reactant 2

HCID 962WaterHCID 671121072-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(4-phenylhepta-1,6-dien-4-yl)thiazolo[5,4-b]pyridine

Product 1

HCID 671118212-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclopent-3-enyl)thiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 2

HCID 12045765Benzylidene(dichloro)(1,3-dimesitylimidazolidin-2-id-2-yl)(tricyclohexylphosphoranyl)rutheniumCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(4-phenylhepta-1,6-dien-4-yl)thiazolo[5,4-b]pyridine (1.07 g, 2.20 mmol) in 44 mL DCM under argon was added tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride (93.3 mg, 0.110 mmol). The reaction mixture became red-brown and was fitted with a water-cooled reflux condenser and heated to reflux. After 5 h, the reaction mixture was cooled, concentrated in vacuo, loaded onto an 80 g ISCO silica gel column, and purified with a gradient of 0-30% EA/hexanes to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-phenylcyclopent-3-enyl)thiazolo[5,4-b]pyridine as an off-white solid. MS (ESI) m/z: Calculated: 458.2; Observed: 459.1 (M++1).

Workup

  1. temperaturecooled
  2. temperaturereflux condenser
  3. temperatureheated to reflux
  4. temperaturethe reaction mixture was cooled
  5. concentrationconcentrated in vacuo
  6. custompurified with a gradient of 0-30% EA/hexanes

Sources & evidence

ORD record
ord-d83895e5e7a1428299fdabc2b9c7134e
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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