Nitrogen → HCID 43145230, compound

HRID 882777Notes

Reaction equation

HRID 882777 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([OH:9])=[O:8].C([O-])([O-])=O.[K+].[K+].[CH3:16][O:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1.N#N>C(O)(C)C.C1(C)C=CC=CC=1.CCOCC>[CH3:16][O:17][C:18]1[CH:23]=[C:22]([C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7]([OH:9])=[O:8])[CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 27396883-Bromothiophene-2-carboxylic acid

Product 1

HCID 43145230HCID 43145230, compoundYield 69.2%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

3-Bromothiophene-2-carboxylic acid (600 mg; 2.9 mmol) was dissolved in isopropanol (7 ml)/toluene (7 ml), followed by the addition of K2CO3 solution (aq; 2M; 9 ml) and 3-methoxybenzeneboronic acid (440 mg; 2.9 mmol). The reaction mixture was deoxygenized with N2 (g) for 3 minutes followed by the addition of tetrakis-(triphenylphosine)-palladium and subsequently heated to 80° C. for 14 h. The mixture was cooled to rt, ether was added and the organic layer was extracted with 2M NaOH-solution. The aq. layer was acidified by the addition of 2M HCl. The product precipitated and was filtered off and dried at high vacuum to give 470 mg of 3-(3-methoxy-phenyl)-thiophene-2-carboxylic acid; LC-MS: tR=0.94 min; [M−H]+=235.27.

Workup

  1. temperatureThe mixture was cooled to rt
  2. extractionthe organic layer was extracted with 2M NaOH-solution
  3. additionThe aq. layer was acidified by the addition of 2M HCl
  4. customThe product precipitated
  5. filtrationwas filtered off
  6. customdried at high vacuum

Sources & evidence

ORD record
ord-9394df42b46841f2bb85a1dcf044342f
Source dataset
uspto-grants-2012_08
Patent number
US08236801B2

Reaction notes

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