Ethanol → 5-Amino-4-(3'-formyl-biphenyl-3-sulfonyl)-thiophene-2-carboxylic acid methyl ester

HRID 723048Notes

Reaction equation

HRID 723048 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([NH2:20])=[C:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15](Br)[CH:14]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4].[CH:21]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1)=[O:22].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>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([NH2:20])=[C:8]([S:10]([C:13]2[CH:14]=[C:15]([C:27]3[CH:26]=[CH:25][CH:24]=[C:23]([CH:21]=[O:22])[CH:28]=3)[CH:16]=[CH:17][CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343563-Formylphenylboronic acidHCID 695864675-Amino-4-(3-bromo-benzenesulfonyl)-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 866011755-Amino-4-(3'-formyl-biphenyl-3-sulfonyl)-thiophene-2-carboxylic acid methyl esterYield 40%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

The procedure as in Example 1: step c was followed using 5-amino-4-(3-bromo-benzenesulfonyl)-thiophene-2-carboxylic acid methyl ester (754.2 mg, 2 mmol, Example 20: step e), 3-formyl phenyl boronic acid (599.7 mg, 4 mmol), Pd(PPh3)4 (462.2 mg, 0.4 mmol), aqueous Na2CO3 (2M, 8 mL, 16 mmol), ethanol (8 mL) and toluene (16 mL). Purification by flash column chromatography (Biotage Flash™ System—40 M SiO2 column) (25% EtOAc in hexanes) of the residue yielded the title compound (317 mg, 40%) as a brown solid. 1H-NMR (CDCl3): δ 10.10 (s, 1H), 8.10–8.17 (m, 2H), 7.92–7.95 (m, 2H), 7.82–7.89 (t, 2H, J=8.1 Hz), 7.58–7.70 (m, 3H), 6.05 (br s, 2H), 3.80 (s, 3H).

Workup

  1. customPurification by flash column chromatography (Biotage Flash™ System—40 M SiO2 column) (25% EtOAc in hexanes) of the residue

Sources & evidence

ORD record
ord-0aedae58789140daa462b6529c12898a
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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