Sodium Carbonate → 4-(6-Amino-2'-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid amide

HRID 2216227Notes

Reaction equation

HRID 2216227 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:12]=[C:13]([C:18]([NH2:20])=[O:19])[S:14][C:15]=2[S:16][CH3:17])(=[O:10])=[O:9])=[CH:4][C:3]=1Br.[CH3:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=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>[NH2:1][C:2]1[C:3]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[CH3:22])=[CH:4][C:5]([S:8]([C:11]2[CH:12]=[C:13]([C:18]([NH2:20])=[O:19])[S:14][C:15]=2[S:16][CH3:17])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 695864864-(4-Amino-3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid amide

Product 1

HCID 695865184-(6-Amino-2'-methyl-biphenyl-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid amideYield 56%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The procedure used in Example 1: step c was followed using 4-(4-amino-3-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid amide ((Example 319: part d) 44 mg, 0.11 mmol), 2-methylphenylboronic acid (54 mg, 0.4 mmol), aq Na2CO3 (2M, 800 μL, 1.6 mmol), and Pd(PPh3)4 (29 mg, 0.025 mmol). Analogous workup and purification by preparative TLC yielded the title compound (24 mg, 56%). 1H-NMR (CDCl3): δ 7.97 (s, 1H), 7.76 (dd, 1H, J=2.3, 8.6 Hz), 7.67 (d, 1H, J=2.3 Hz), 7.32 (m, 2H), 7.28 (m, 1H), 7.16 (m, 1H), 6.76 (d, 1H, J=8.6 Hz), 4.11 (s, 2H), 2.58 (s, 3H), 2.13 (s, 3H).

Workup

  1. customAnalogous workup and purification by preparative TLC

Sources & evidence

ORD record
ord-082259eb1af146999be4dd04c41ad1be
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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