Triethylamine → 6-(5-Methoxy-benzofuran-2-yl)-nicotinamide

HRID 501043Notes

Reaction equation

HRID 501043 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9](B(O)O)=[CH:8][C:7]=2[CH:14]=1.Br[C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH2:22])=[O:21])=[CH:18][N:17]=1.CCN(CC)CC>CCO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:16]3[CH:24]=[CH:23][C:19]([C:20]([NH2:22])=[O:21])=[CH:18][N:17]=3)=[CH:8][C:7]=2[CH:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 184194566-BromonicotinamideHCID 22221596(5-Methoxy-1-benzofuran-2-yl)boronic acid

Product 1

HCID 250149326-(5-Methoxy-benzofuran-2-yl)-nicotinamideYield 31.7%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

5-methoxybenzofuran boronic acid (1.2 mmol), 6-bromonicotinamide (1.0 mmol), Pd(PPh3)2Cl2 (0.024 mmol) and NEt3 (317 μL) were mixed in EtOH (10 mL) in a 20 mL microwave vial. The mixture was stirred at 140° C. for 10 min in a microwave reactor. The mixture was filtered, the obtained precipitate was washed with water and EtOAc and dried under vacuum to afford the title compound (85 mg). 1H NMR δ ppm 9.14 (d, 1 H) 8.42 (dd, 1 H) 7.97-8.25 (m, 2 H) 7.63-7.80 (m, 2 H) 7.58 (d, 1 H) 7.22 (d, 1 H) 6.98 (dd, 1H) 3.81 (s, 3 H); MS m/z 269 (M+H).

Workup

  1. filtrationThe mixture was filtered
  2. washthe obtained precipitate was washed with water and EtOAc
  3. customdried under vacuum

Sources & evidence

ORD record
ord-e7a46a32da9b47ad8262f29699fe97bd
Source dataset
uspto-grants-2010_08
Patent number
US07772256B2

Reaction notes

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