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

HRID 2204837Notes

Reaction equation

HRID 2204837 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-69b4cbe7869c477e8be5d3c4f52ce32b
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Reaction notes

Loading…