Potassium Carbonate → N-[4-(4-formylphenyl)thiophen-2-ylmethyl]-N-methylbenzamide

HRID 2426290Notes

Reaction equation

HRID 2426290 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].Br[C:13]1[CH:14]=[C:15]([CH2:18][N:19]([CH3:28])[C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:13]2[CH:14]=[C:15]([CH2:18][N:19]([CH3:28])[C:20](=[O:27])[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[S:16][CH:17]=2)=[CH:5][CH:4]=1)=[O:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 47042144N-[(4-Bromo-2-thienyl)methyl]-N-methylbenzamide

Product 1

HCID 86017444N-[4-(4-formylphenyl)thiophen-2-ylmethyl]-N-methylbenzamideYield 79.5%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

3 g (20 mmol) of 4-formylbenzeneboronic acid are added to a solution of 4.75 g (15 mmol) of N-(4-bromothiophen-2-ylmethyl)-N-methylbenzamide in 60 ml of toluene, followed by dropwise addition of 5.5 g (40 mmol) of aqueous potassium carbonate solution. The reaction medium is degassed, 530 mg (0.5 mmol) of tetrakis (triphenylphosphine) palladium are then added and the medium is heated at 80° C. for 18 hours. After extraction with ethyl acetate and washing with water, the organic phase is dried over magnesium sulfate, filtered and concentrated under vacuum. The residue obtained is purified by chromatography on a column of silica eluted with a 1/1 heptane/ethyl acetate mixture. 4 g (78%) of N-[4-(4-formylphenyl)thiophen-2-ylmethyl]-N-methyl-benzamide are obtained.

Workup

  1. customThe reaction medium is degassed
  2. extractionAfter extraction with ethyl acetate
  3. washwashing with water
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with a 1/1 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-9d6511eabd6b442a88bbc627f9b580fe
Source dataset
uspto-grants-2011_06
Patent number
US07968560B2

Reaction notes

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