Potassium Phosphate, Tribasic → HCID 59455105, compound

HRID 1400545Notes

Reaction equation

Br[CH:2]=[C:3]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)[CH3:4].P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O.[Cl:27][C:28]1[CH:36]=[CH:35][C:34]2[NH:33][C:32]3[CH2:37][CH2:38][N:39]([C:41]([O:43][CH2:44][C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[O:42])[CH2:40][C:31]=3[C:30]=2[CH:29]=1>CN(C=O)C.[Cu]I>[Cl:27][C:28]1[CH:36]=[CH:35][C:34]2[N:33](/[CH:2]=[C:3](/[C:5]3[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=3)\[CH3:4])[C:32]3[CH2:37][CH2:38][N:39]([C:41]([O:43][CH2:44][C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[O:42])[CH2:40][C:31]=3[C:30]=2[CH:29]=1

Participants

Conditions

Temperature: 80 °C

Procedure

4-(1-Bromoprop-1-en-2-yl)pyridine (237 mg, 1.2 mmol) was dissolved in DMF and potassium phosphate (424 mg, 2 mmol) was added followed by the addition of copper (I)iodide (19 mg, 0.1 mmol) and L-proline (23 mg, 0.2 mmol). Benzyl 8-chloro-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (340 mg, 1 mmol) was added and nitrogen gas purged for 2 min. The reaction mixture was heated at 80° C. overnight. The reaction mixture was cooled to RT and water (20 mL) was added. The compound was extracted with EtOAc (3×50 mL). The organic layer was washed with water (2×50 mL) and compound was purified through reverse phase HPLC. Yield: 13.4 mg. 1H NMR (CDCl3, free base) δ (ppm): 8.64 (d, 2H), 7.25-7.15 (m, 8H), 7.18 (d, 1H), 7.05 (m, 2H), 5.20 (s, 2H), 4.70 (s, 2H), 3.90 (m, 2H), 2.78 (m, 2H), 1.98 (s, 3H).

Workup

customnitrogen gas purged for 2 min
temperatureThe reaction mixture was cooled to RT
additionwater (20 mL) was added
extractionThe compound was extracted with EtOAc (3×50 mL)
washThe organic layer was washed with water (2×50 mL) and compound
customwas purified through reverse phase HPLC

Sources & evidence

ORD record: ord-cf3d8ae565e245d5a79196cd2eb1da3d
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906925B2

Reaction notes

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