Triethylamine → HCID 86631778, compound

HRID 1051323Notes

Reaction equation

HRID 1051323 reaction equation
[N:1]1[C:2]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.Br[C:45]1[CH:50]=[CH:49][N:48]=[CH:47][CH:46]=1>O1CCOCC1.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:48]1[CH:49]=[CH:50][C:45]([C:3]2[N:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]3=[N:1][C:2]=2[C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)=[CH:46][CH:47]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 142684-BromopyridineHCID 8209634-imidazo[1,2-a]pyridin-2-ylbenzaldehyde

Product 1

HCID 86631778HCID 86631778, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

0.2 g (0.9 mM) 4-imidazo[1,2-a]pyridin-2-ylbenzaldehyde (prepared as described by Sundberg et al.; J. Heterocyclic Chem., 25, 129, 1988) is dissolved in 5 mL of Dioxane. To this is added CsCO3 (1.1 eq), palladium acetate (8 mol %), triphenyl phosphine (16 mol %), triethylamine (2 eq) and 4-bromo-pyridine (1.4 eq). The reaction mixture is heated (microwave) for 45 min at 100° C. The reaction mixture is cooled to RT, diluted with DCM. The organic layer is washed with water, dried and concentrated. The crude product purified by column chromatography to obtain the desired compound.

Workup

  1. temperatureThe reaction mixture is cooled to RT
  2. washThe organic layer is washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product purified by column chromatography

Sources & evidence

ORD record
ord-047246ed6a494eae954aa6e1e16fb3f1
Source dataset
uspto-grants-2016_07
Patent number
US09387204B2

Reaction notes

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