Potassium Phosphate, Tribasic → HCID 59455014, compound

HRID 1400581Notes

Reaction equation

Br[CH:2]=[C:3]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[N:9][CH:10]=1)[CH3:4].P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O.[CH3:29][N:30]1[CH2:43][CH2:42][C:33]2[NH:34][C:35]3[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][C:40]=3[C:32]=2[CH2:31]1>CN(C=O)C.[Cu]I.O>[CH3:12][O:11][C:8]1[N:9]=[CH:10][C:5](/[C:3](/[CH3:4])=[CH:2]/[N:34]2[C:35]3[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][C:40]=3[C:32]3[CH2:31][N:30]([CH3:29])[CH2:43][CH2:42][C:33]2=3)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 85 °C

Procedure

5-(-1-Bromoprop-1-en-2-yl)-2-methoxypyridine (50 mg, 0.25 mmol) was dissolved in DMF (2 mL). Potassium phosphate (106 mg, 0.5 mmol) was added followed by copper (I) iodide (4 mg, 0.02 mmol) and L-proline (5 mg, 0.04 mmol). 2,3,4,5-Tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole (50 mg, 0.25 mmol) was added under nitrogen (Nitrogen purged for 2 min). The reaction mixture was stirred at 85° C. overnight. Water (15 mL) was added and compound extracted with EtOAc (3×30 mL). The organic layer was concentrated under vacuum and purified through reverse phase chromatography. Yield: 3.87 mg (TFA salt). 1H NMR (CD3OD, TFA salt) δ (ppm): 8.30 (s, 1H), 7.90 (d, 1H), 7.20 (s, 1H), 7.02 (d, 1H), 6.99 (d, 1H), 4.62 (m, 1H), 4.30 (m, 1H), 3.86 (s, 3H), 3.78 (m, 1H), 3.50 (m, 1H), 3.05 (m, 2H), 3.02 (s, 3H), 2.38 (s, 3H), 1.82 (s, 3H).

Workup

extractioncompound extracted with EtOAc (3×30 mL)
concentrationThe organic layer was concentrated under vacuum
custompurified through reverse phase chromatography

Sources & evidence

ORD record: ord-bac4c15abea14d7eaef31acdb703eae8
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906925B2

Reaction notes

Loading…