Sodium Carbonate → 5-Amino-4-cyano-3-(2'methylsulfanyl-biphenyl-4-yl)-thiophene-2-carboxylic acid ethyl ester

HRID 1990086Notes

Reaction equation

HRID 1990086 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([NH2:20])=[C:9]([C:18]#[N:19])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1)=[O:5])[CH3:2].[CH3:21][S:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([NH2:20])=[C:9]([C:18]#[N:19])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[S:22][CH3:21])=[CH:13][CH:12]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27735432-(Methylthio)benzeneboronic acidHCID 685218625-Amino-4-cyano-3-(4-iodo-phenyl)-thiophene-2-carboxylic acid ethyl ester

Product 1

HCID 685240485-Amino-4-cyano-3-(2'methylsulfanyl-biphenyl-4-yl)-thiophene-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Combine 5-amino-4-cyano-3-(4-iodo-phenyl)-thiophene-2-carboxylic acid ethyl ester (0.829 mmol) in dioxane and add 2-(methylthio)phenylboronic acid, tetrakis(triphenylphosphine)palladium (0), and 1.4 ml of 2M sodium carbonate solution and heat to reflux. After 3 hours, purification by radial chromatography (6000 micron Si plate) eluting with 10-20% ethylacetate/methylene chloride provides the title compound: 1H NMR (400 MHz, CDCl3) δ 7.49-7.19 (m, 8H), 5.26 (s, 2H), 4.17 (q, 2H, J=7.2 Hz), 2.38 (s, 3H), 1.18 (t, 3H, J=7.0 Hz), MS found (M+1) 395.1.

Workup

  1. temperatureheat to reflux
  2. custompurification by radial chromatography (6000 micron Si plate)
  3. washeluting with 10-20% ethylacetate/methylene chloride

Sources & evidence

ORD record
ord-30fc145f6fd74b86a7292c9102f70c46
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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