Triethylamine → 4-(5-amino-6-(5-(2-vinylphenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-N,N-dimethylbenzamide

HRID 78614Notes

Reaction equation

HRID 78614 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:20]2[CH:30]=[CH:29][C:23]([C:24]([N:26]([CH3:28])[CH3:27])=[O:25])=[CH:22][CH:21]=2)=[N:6][C:7]=1[C:8]1[O:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2I)=[N:11][N:12]=1.F[C:32]([B])=[C:33](F)F.[K].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CCC=1>C(O)CC.Cl[Pd]Cl.[Fe].ClCCl>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:20]2[CH:30]=[CH:29][C:23]([C:24]([N:26]([CH3:28])[CH3:27])=[O:25])=[CH:22][CH:21]=2)=[N:6][C:7]=1[C:8]1[O:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:32]=[CH2:33])=[N:11][N:12]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 3524393Cyclopenta-1,4-dien-1-yl(diphenyl)phosphaneHCID 594717314-[5-amino-6-[5-(2-iodophenyl)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N,N-dimethyl-benzamideHCID 87394693Potassium trifluoro-vinyl-boron

Product 1

HCID 594721584-(5-amino-6-(5-(2-vinylphenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-N,N-dimethylbenzamideYield 53.5%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 24290Palladium ChlorideCatalystHCID 10311-PropanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4-[5-amino-6-[5-(2-iodophenyl)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N,N-dimethyl-benzamide (100 mg, 0.1952 mmol), potassium trifluoro-vinyl-boron (31.37 mg, 0.2342 mmol), triethyl amine (81.63 μL, 0.5857 mmol) and cyclopenta-1,4-dien-1-yl(diphenyl)phosphane; dichloromethane; dichloropalladium; iron (31.88 mg, 0.03904 mmol) in propanol (2.000 mL) was degassed and flushed with nitrogen (3×) and the resulting solution heated at 100° C. for 1 h. The reaction mixture cooled to room temperature and concentrated in vacuo. The residue was purified by column chromatography on silica eluting with ethyl acetate. Product fractions were combined and concentrated in vacuo to leave the product as a yellow solid (43.1 mg, 53% yield); 1H NMR (400.0 MHz, DMSO) d 2.97 (m, 6H), 5.51 (m, 1H), 5.98 (m, 1H), 7.54 (m, 2H), 7.58-7.70 (m, 3H), 7.78 (br s, 2H), 7.89 (m, 1H), 8.06 (m, 2H) and 9.00 (s, 1H) ppm; MS (ES+) 413.15

Workup

  1. customflushed with nitrogen (3×)
  2. temperatureThe reaction mixture cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica eluting with ethyl acetate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-026549129d1342c9879ddaad222e705d
Source dataset
uspto-grants-2014_09
Patent number
US08841308B2

Reaction notes

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