Potassium Phosphate, Tribasic → HCID 59455230, compound

HRID 1400591Notes

Reaction equation

Br[CH:2]=[C:3]([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O.[CH3:32][N:33]1[CH2:46][CH2:45][C:36]2[NH:37][C:38]3[CH:39]=[CH:40][C:41]([CH3:44])=[CH:42][C:43]=3[C:35]=2[CH2:34]1>CN(C=O)C.[Cu]I>[CH3:32][N:33]1[CH2:46][CH2:45][C:36]2[N:37](/[CH:2]=[C:3](/[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)\[C:10]3[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=3)[C:38]3[CH:39]=[CH:40][C:41]([CH3:44])=[CH:42][C:43]=3[C:35]=2[CH2:34]1

Participants

Conditions

Temperature: 85 °C

Procedure

4-(2-Bromo-1-phenylvinyl)pyridine (310 mg, 1.1 mmol) was dissolved in DMF (5 mL) and potassium phosphate (424 mg, 2 mmol) was added followed by copper (I) iodide (19 mg, 0.1 mmol) and L-proline (23 mg, 0.2 mmol). 2,3,4,5-Tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole (200 mg, 1 mmol) was added and the mixture purged with nitrogen for 2 min. The reaction mixture was stirred at 85° C. overnight. Water was added and the solid mass was filtered under vacuum. The crude product was purified on silica gel (100-200 mesh) using 0-10% MeOH:DCM as eluent. The compound was further purified through reverse phase HPLC. Yield: 28 mg. 1H NMR (CD3OD, free base) δ (ppm): 8.40 (d, 2H), 7.39 (m, 3H), 7.32 (d, 2H), 7.16 (s, 1H), 7.10 (s, 1H), 6.90 (m, 4H), 3.62 (s, 2H), 2.68 (m, 2H), 2.50 (m, 5H), 2.39 (s, 3H).

Workup

customthe mixture purged with nitrogen for 2 min
additionWater was added
filtrationthe solid mass was filtered under vacuum
customThe crude product was purified on silica gel (100-200 mesh)
customThe compound was further purified through reverse phase HPLC

Sources & evidence

ORD record: ord-b7add243303e45ce90711e87306ee353
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906925B2

Reaction notes

Loading…