1,2-Dimethoxyethane → HCID 66854772, compound

HRID 2282218Notes

Reaction equation

HRID 2282218 reaction equation
[CH3:1][C:2]1[C:10]([C:11]2[S:12][C:13]([C:24]([O:26][CH3:27])=[O:25])=[C:14](OS(C(F)(F)F)(=O)=O)[N:15]=2)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:28][C:29]1(C)[C:33](C)(C)OB(CC=C)O1.C(=O)([O-])[O-].[Cs+].[Cs+].COCCOC>O>[CH3:1][C:2]1[C:10]([C:11]2[S:12][C:13]([C:24]([O:26][CH3:27])=[O:25])=[C:14]([CH2:33][CH:29]=[CH2:28])[N:15]=2)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 27631714,4,5,5-Tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolaneHCID 86649588HCID 86649588, compound

Product 1

HCID 66854772HCID 66854772, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using methyl 2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-4-{[(trifluoromethyl)sulfonyl]oxy}-1,3-thiazole-5-carboxylate (1.5 g, 3.6 mmol) produced in Example 13-B (ii), 4,4,5,5-tetramethyl-2-prop-2-en-1-yl-1,3,2-dioxaborolane (897 mg, 5.3 mmol), [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex (180 mg, 0.22 mmol), cesium carbonate (3.5 g, 11 mmol), 1,2-dimethoxyethane (50 mL) and water (3 mL) as starting materials and in the same manner as in Example 13-B (iii), the title compound (815 mg, 73%) was obtained as a yellow solid.

Sources & evidence

ORD record
ord-2033051b3def40278c7593f818a1621b
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

Loading…