5-Bromonicotinamide → 5-(4-Formylphenyl)-3-pyridinecarboxamide

HRID 471862

Reaction equation

HRID 471862 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].[CH:11]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)=[O:12].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C([O-])([O-])=O.[K+].[K+]>C(O)CCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:10]=[C:6]([C:7]([NH2:9])=[O:8])[CH:5]=[N:4][CH:3]=2)=[CH:15][CH:14]=1)=[O:12]

Participants

7

Reactant 4

HCID 18085-BromonicotinamideHCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 582762725-(4-Formylphenyl)-3-pyridinecarboxamide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 2631-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromonicotinamide (0.201 g; 1.00 mmol), 4-formylphenyl boronic acid (0.180 g; 1.2 mmol), Pd(OAc)2 (0.0022 g; 0.010 mmol), S-Phos (0.0082 g; 0.020 mmol) and K2CO3 (0.345 g; 2.5 mmol) in n-butanol (3 mL) was sparged with nitrogen ca. 10 min, then heated at 80° C. for 1 h. Upon cooling, the mixture was poured into water, layered with Et2O and sonicated at room temperature ca. 5 min. Solid was collected by filtration, and the cake was air-dried on the filter, affording the title compound as a colorless solid which was used without further purification. LC/MS (method A) 1.57 min; m/z 227 (M+H).

Workup

  1. customwas sparged with nitrogen ca. 10 min
  2. temperatureUpon cooling
  3. additionthe mixture was poured into water
  4. customsonicated at room temperature ca. 5 min
  5. filtrationSolid was collected by filtration
  6. customthe cake was air-dried on the filter

Sources & evidence

ORD record
ord-b963c5927eb24f5f8e38bed2904a6c2e
Source dataset
uspto-grants-2014_01
Patent number
US08633175B2

Linked notes

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