Sodium Carbonate → tert-butyl N-[4-[3-(2-chlorophenyl)-5-hydroxyphenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 723044Notes

Reaction equation

HRID 723044 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]([C:10]1[S:11][C:12]([S:26][CH3:27])=[C:13]([S:15]([C:18]2[CH:23]=[C:22]([OH:24])[CH:21]=[C:20](Br)[CH:19]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2].[Cl:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]([C:10]1[S:11][C:12]([S:26][CH3:27])=[C:13]([S:15]([C:18]2[CH:19]=[C:20]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[Cl:29])[CH:21]=[C:22]([OH:24])[CH:23]=2)(=[O:17])=[O:16])[CH:14]=1)=[NH:9])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 140043482tert-butyl N-[4-(3-bromo-5-hydroxyphenyl)sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

Product 1

HCID 145857663tert-butyl N-[4-[3-(2-chlorophenyl)-5-hydroxyphenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamateYield 24%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Following the procedure outlined in Example 1: step c, {[4-(3-bromo-5-hydroxy-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (80 mg, 0.158 mmol) was reacted with 2-chlorophenylboronic acid (98.6 mg, 0.631 mmol), Na2CO3 (134 mg, 1.26 mmol), and Pd(PPh3)4 (45.5 mg, 0.039 mmol). Aqueous workup followed by SiO2 flash chromatography yielded the title compound (20 mg, 24%).

Sources & evidence

ORD record
ord-b7c17c1fd905464eb5d0282a21ac7cfb
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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