Ethanol → 4-(6-Amino-5-o-tolyl-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid amide
Reaction equation
[NH2:1][C:2]1[N: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.[C:22]1([CH3:37])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1C1C=CC=CC=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C(O)C>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.C1(C)C=CC=CC=1>[NH2:1][C:2]1[N: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]=1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH3:37]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
The procedure as in Example 1: step c was followed using 4-(6-amino-5-bromo-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid amide (25 mg, 0.06 mmol, Example 120: step a), o-tolyl phenyl boronic acid (33 mg, 0.25 mmol), Pd(PPh3)4 (14 mg, 0.01 mmol), aqueous Na2CO3 (2M, 0.4 mL), ethanol (0.4 mL) and toluene (0.8 mL). Purification by preparative SiO2 chromatography (25% EtOAc in hexanes) of the residue yielded the title compound (7.4 mg, 32%) as a brown solid. ESI-MS (m/z): Calcd. for C18H17N3O3S3: 420.0 (M+H); found: 420.2.
Workup
- customPurification by preparative SiO2 chromatography (25% EtOAc in hexanes) of the residue
Sources & evidence
- ORD record
- ord-0ea340c0aecf4cf6aa27c46c31488edf
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109354B2
Reaction notes
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