Dimethylformamide → HCID 59454928, compound

HRID 1400539Notes

Reaction equation

[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[NH:16]1[CH2:23][CH2:22]C[C@H:17]1C(O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:32][C:33]1N=CC=N[CH:38]=1.C[N:40]([CH:42]=O)[CH3:41]>[Cu]I>[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[N:6](/[CH:32]=[C:33](/[C:41]3[CH:17]=[N:16][C:23]([CH3:22])=[CH:42][N:40]=3)\[CH3:38])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido (4,3-b) indole (70 mg, 0.35 mmol), copper (I) iodide (6.6 mg, 0.035 mmol), L-proline (8.05 mg, 0.07 mmol), Potassium phosphate tribasic (148 mg, 0.7 mmol) were dissolved in DMF (3 mL) and stirred for 5 min. 2-(2-bromo-1-methyl-vinyl))-5-methylpyrazine (81 mg, 0.385 mmol) was added and nitrogen gas purged into the reaction mixture for a min. The reaction mixture was stirred at RT for 5 min followed by heating at 90° C. for 14 h. After completion of the reaction, DMF was evaporated. Water was added to the reaction mixture and the mixture filtered to obtain the solid crude, which was purified by reverse phase HPLC to obtain 20 mg desired product. 1H NMR (CDCl3, free base) δ (ppm): 8.70 (s, 1H), 8.50 (s, 1H), 7.60 (s, 1H), 7.24 (s, 1H), 7.05 (m, 2H), 3.80 (s, 2H), 2.90 (m, 4H), 2.64 (s, 3H), 2.62 (s, 3H), 2.42 (s, 3H), 2.14 (s, 3H).

Workup

customnitrogen gas purged into the reaction mixture for a min
stirringThe reaction mixture was stirred at RT for 5 min
customAfter completion of the reaction, DMF
customwas evaporated
additionWater was added to the reaction mixture
filtrationthe mixture filtered
customto obtain the solid crude, which
customwas purified by reverse phase HPLC

Sources & evidence

ORD record: ord-03d378b1028c47fca2868e88f4ffde4a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906925B2

Reaction notes

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