Potassium Phosphate, Tribasic → (E)-10-methyl-7-(2-(6-methylpyridin-3-yl)prop-1-enyl)-2,3,5,6,7,11c-hexahydro-1H-indolizino[7,8-b]indole

HRID 1497960Notes

Reaction equation

[CH3:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH2:9][CH2:8][N:7]4[CH2:15][CH2:16][CH2:17][CH:6]4[C:5]=3[C:4]=2[CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O.Br[CH:35]=[C:36]([C:38]1[CH:39]=[CH:40][C:41]([CH3:44])=[N:42][CH:43]=1)[CH3:37]>CN(C=O)C.O.[Cu](I)I>[CH3:1][C:2]1[CH:14]=[CH:13][C:12]2[N:11](/[CH:35]=[C:36](/[C:38]3[CH:43]=[N:42][C:41]([CH3:44])=[CH:40][CH:39]=3)\[CH3:37])[C:10]3[CH2:9][CH2:8][N:7]4[CH:6]([C:5]=3[C:4]=2[CH:3]=1)[CH2:17][CH2:16][CH2:15]4

Participants

Conditions

Temperature: 120 °C

Procedure

To a degassed solution of 9-methyl-2,3,4,5,6,10c-hexahydro-1H-3a,6-diaza-cyclopenta[c]fluorene (50 mg, 0.22 mmol), potassium phosphate (100 mg, 0.462 mmol), L-proline (5 mg, 0.022 mmol) and copper iodide (5 mg, 0.044 mmol) in DMF (1 mL) was added 5-(2-bromo-1-methyl-vinyl)-2-methyl-pyridine (80 mg, 0.375 mmol). The reaction mixture was stirred at 120° C. for 20 h. The progress of reaction was monitored by TLC and LCMS. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (3×10 mL). The organic layer was washed with water (3×10 mL), followed by brine (15 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by reverse phase HPLC;

Workup

customThe progress of reaction
extractionextracted with EtOAc (3×10 mL)
washThe organic layer was washed with water (3×10 mL)
dry with materialdried over anhydrous Na2SO4
customevaporated under reduced pressure
customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-8a425e06907b438b8d7465dd1ac69d4e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199996B2

Reaction notes

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