Potassium Carbonate → HCID 67111995, compound

HRID 1177412Notes

Reaction equation

O.[C:2]1([C:8](B(O)O)=[CH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:14]1[N:19]=[C:18]2[S:20][C:21]([CH3:23])=[N:22][C:17]2=[CH:16][CH:15]=1.O1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:23][C:21]1[S:20][C:18]2[C:17]([N:22]=1)=[CH:16][CH:15]=[C:14]([C:8]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[CH2:9])[N:19]=2

Participants

Conditions

Temperature: 90 °C

Procedure

A 1000 mL rbf was charged with 1-phenylvinylboronic acid hydrate (36.7 g, 221 mmol), (amphos)2PdCl2 (3.26 g, 4.60 mmol), and 5-chloro-2-methylthiazolo[5,4-b]pyridine (34.0 g, 184 mmol) under argon. Dioxane (200 mL) was added followed by a solution of potassium carbonate (61.1 g, 442 mmol) in 60 mL water, and the reaction was fitted with a water cooled reflux condenser and flushed with argon. The resulting slurry was heated to 90° C. for 3 h. The reaction mixture was allowed to cool, and was diluted with 200 mL MTBE and water. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a thick brown oil. The oil was purified by silica gel chromatography, 0-30% EA/hexanes to give 2-methyl-5-(1-phenylvinyl)thiazolo[5,4-b]pyridine as a brown oil. MS (ESI) m/z: calculated: 252.1; Observed: 253.1 (M++1).

Workup

temperaturecooled
temperaturereflux condenser
customflushed with argon
temperatureto cool
additionwas diluted with 200 mL MTBE and water
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customto give a thick brown oil
customThe oil was purified by silica gel chromatography, 0-30% EA/hexanes

Sources & evidence

ORD record: ord-f6cb1ce895bf43a984a1e39365270a7b
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

Loading…