1,2-Dimethoxyethane → HCID 66854661, compound

HRID 2282177Notes

Reaction equation

HRID 2282177 reaction equation
FC1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C:16]3[C:17]([CH3:25])=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=34)[S:11][C:12]=2[C:13](N)=[O:14])[CH:5]=[CH:6]C=1.[O:26]1C=CC(B(O)O)=[CH:27]1.C(=O)([O-])[O-:35].[Cs+].[Cs+].COCCOC>O>[O:35]1[CH:6]=[CH:5][C:4]([C:8]2[N:9]=[C:10]([C:16]3[C:17]([CH3:25])=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=34)[S:11][C:12]=2[C:13]([O:26][CH3:27])=[O:14])=[CH:3]1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10796Cesium carbonateHCID 2734358Furan-3-boronic acidHCID 66856818HCID 66856818, compound

Product 1

HCID 66854661HCID 66854661, compoundYield 93.4%

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 (300 mg, 0.71 mmol) produced in Example 13-B (ii), furan-3-ylboronic acid (160 mg, 1.4 mmol), [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex (70 mg, 0.086 mmol), cesium carbonate (830 mg, 2.6 mmol), 1,2-dimethoxyethane (20 mL) and water (0.5 mL) as starting materials and in the same manner as in Example 13-B(iii), the title compound (225 mg, 93%) was obtained as a yellow solid.

Sources & evidence

ORD record
ord-cd0d1669c58a480da256ef9d8bef54de
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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