N-tert-butyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide → Methyl 3'-tert-butylsulfamoyl-5-formyl-6-(2-methoxyethoxymethoxy)-biphenyl-3-carboxylate

HRID 1622116Notes

Reaction equation

HRID 1622116 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:19]=[O:20])[C:11]=1[O:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[C:5]([O:7][CH3:8])=[O:6].[C:21]([NH:25][S:26]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=1)(=[O:28])=[O:27])([CH3:24])([CH3:23])[CH3:22]>>[C:21]([NH:25][S:26]([C:29]1[CH:30]=[C:31]([C:2]2[C:11]([O:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:10]([CH:19]=[O:20])[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=2)[CH:32]=[CH:33][CH:34]=1)(=[O:28])=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

3

Reactant 2

HCID 58169119N-tert-butyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamideHCID 86607700Methyl 3-bromo-5-formyl-4-(2-methoxyethoxymethoxy)-benzoate

Product 1

HCID 86607699Methyl 3'-tert-butylsulfamoyl-5-formyl-6-(2-methoxyethoxymethoxy)-biphenyl-3-carboxylateYield 78.2%

Procedure

Proceeding as in Reference 19, but substituting methyl 3-bromo-5-formyl-4-(2-methoxyethoxymethoxy)-benzoate (2.00 g, 5.76 mmol, 1.0 eq.) and N-tert-butyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzenesulfonamide (1.95 g, 5.76 mmol, 1.0 eq.), gave methyl 3′-tert-butylsulfamoyl-5-formyl-6-(2-methoxyethoxymethoxy)-biphenyl-3-carboxylate (2.16 g) as a yellow gum.

Sources & evidence

ORD record
ord-0d8126a784454432b96c40d41a7144d6
Source dataset
uspto-grants-2014_07
Patent number
US08778625B2

Reaction notes

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