Dichloromethane → 2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylvinyl)thiazolo[4,5-c]pyridine

HRID 1177515Notes

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[CH:20]=[C:19](Cl)[N:18]=[CH:17][C:16]=3[N:22]=2)=[C:9]([F:23])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[C:30]1([C:36](B(O)O)=[CH2:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(Cl)Cl>O1CCOCC1.O>[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[CH:20]=[C:19]([C:36]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH2:37])[N:18]=[CH:17][C:16]=3[N:22]=2)=[C:9]([F:23])[CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A slurry of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-chlorothiazolo[4,5-c]pyridine (1.00 g, 2.85 mmol), (Amphos)2PdCl2 (0.0505 g, 0.0713 mmol), potassium carbonate (1.34 g, 9.69 mmol), 1-phenylvinylboronic acid (0.928 g, 6.27 mmol) in 12 mL dioxane and 3 mL water was heated to 60° C. overnight in a sealed tube. Additional (Amphos)2PdCl2 (0.0505 g, 0.0713 mmol) was added and the temperature raised to 90° C. After 3 h, the homogeneous reaction mixture was cooled and treated with water and DCM. The organic layer was extracted with DCM, and combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo. The solid was suspended in MTBE and filtered to give 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-(1-phenylvinyl)-thiazolo[4,5-c]pyridine as an off-white solid. MS (ESI) m/z: calculated: 418.1; Observed: 419.0 (M++1).

Workup

temperaturethe homogeneous reaction mixture was cooled
extractionThe organic layer was extracted with DCM
dry with materialcombined organics were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
filtrationfiltered

Sources & evidence

ORD record: ord-5c2e13e1dbad4d83bf654b004ee4571a
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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