Sodium Carbonate → HCID 66690111, compound

HRID 1020439Notes

Reaction equation

HRID 1020439 reaction equation
Br[C:2]1[C:3]([CH3:20])=[C:4]([CH:17]=[CH:18][CH:19]=1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:6].C(=O)([O-])[O-].[Na+].[Na+].[CH3:27][O:28][C:29]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:30]=1B(O)O>O1CCOCC1.O>[CH3:20][C:3]1[C:2]([C:32]2[CH:31]=[CH:30][C:29]([O:28][CH3:27])=[CH:34][C:33]=2[O:35][CH3:36])=[CH:19][CH:18]=[CH:17][C:4]=1[C:5]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[O:6]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343412,4-Dimethoxybenzeneboronic acidHCID 65544462HCID 65544462, compound

Product 1

HCID 66690111HCID 66690111, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

The procedure of the step 1 in Example 92 was repeated except that the methyl 6-(3-bromo-2-methylbenzamido)hexanoate (34 mg, 0.10 mmol), tetrakis(triphenylphosphin)palladium (12 mg, 0.010 mmol), sodium carbonate (21 mg, 0.20 mmol), and 2,4-dimethoxyphenyl boronic acid (27 mg, 0.15 mmol) instead of phenyl boronic acid were dissolved in 3 mL of dioxane/H2O (4:1, v/v) to obtain the title compound (31 mg, 80%).

Sources & evidence

ORD record
ord-e7e8e8e16ff549b483d0593af8770c7c
Source dataset
uspto-grants-2014_05
Patent number
US08716326B2

Reaction notes

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