Triethylamine → HCID 86720257, compound

HRID 539580Notes

Reaction equation

HRID 539580 reaction equation
[O:1]1[CH2:4][CH:3]([NH2:5])[CH2:2]1.C(N(CC)CC)C.Br[C:14]1[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][N:15]=1>C(O)(C)C>[O:1]1[CH2:4][CH:3]([NH:5][C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][N:15]=2)[CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 50057186-Bromopyridine-3-carbonitrileHCID 98339233-Oxetanamine

Product 1

HCID 86720257HCID 86720257, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a microwave vial, oxetan-3-amine (125 mg, 1.736 mmol), triethylamine (526 mg, 5.21 mmol) were added to a solution of 2-bromo-5-cyanopyridine (317 mg, 1.736 mmol) in isopropanol (3 mL). The vial was capped and irradiated in a microwave oven at 120° C. for 5 h. The reaction mixture was partitioned between ethyl acetate (10 mL) and water (10 mL). The organic layer was washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure. The resulting crude product was purified by column chromatography over silica gel (chloroform/MeOH, 0-5% EtOAc) to afford 75 mg (25%) of 6-(oxetan-3-ylamino)nicotinonitrile (I-25) as an off-white solid. 1H NMR (400 MHz, DMSO) δ 8.36 (s, 1H), 7.58-7.61 (dd, J=1.9, 6.9 Hz, 1H), 6.39 (d, J=8.7 Hz, 2H), 5.37 (br. s, 1H), 4.91-5.06 (m, 3H), 4.54-4.57 (m, 2H); ESI-LC/MS (m/z): [M+H]+ 176.2, RT 1.65 min.

Workup

  1. customThe vial was capped
  2. customirradiated in a microwave oven at 120° C. for 5 h
  3. customThe reaction mixture was partitioned between ethyl acetate (10 mL) and water (10 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed under reduced pressure
  7. customThe resulting crude product was purified by column chromatography over silica gel (chloroform/MeOH, 0-5% EtOAc)

Sources & evidence

ORD record
ord-8fecf9064ac0466daba77054a0740390
Source dataset
uspto-grants-2014_10
Patent number
US08871754B2

Reaction notes

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