Potassium Phosphate, Tribasic → HCID 46200049, compound

HRID 1401647Notes

Reaction equation

Br[CH:2]=[C:3]([C:5]1[CH:15]=[CH:14][C:8]([C:9]([N:11]([CH3:13])[CH3:12])=[O:10])=[CH:7][CH:6]=1)[CH3:4].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:5]3[CH:15]=[CH:14][C:8]([C:9]([N:11]([CH3:13])[CH3:12])=[O:10])=[CH:7][CH:6]=3)\[CH3:4])[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-(1-Bromoprop-1-en-2-yl)-N,N-dimethylbenzamide (264 mg, 1 mmol) was dissolved in DMF (2 mL). 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 under nitrogen for 2 min. The reaction mixture was stirred at 85° C. overnight. Ice water (5 mL) was added and the resulting solid mass was filtered to obtain the crude compound which was purified on silica gel chromatography (100-200 mesh) using 0-7% MeOH: DCM as eluent. Yield: 60 mg. 1H NMR (CD3OD, HCl salt) δ (ppm): 7.76 (d, 2H), 7.50 (d, 2H), 7.30 (s, 1H), 7.10 (m, 3H), 4.75 (d, 1H), 4.40 (d, 1H), 3.84 (m, 1H), 3.60 (m, 1H), 3.18 (m, 2H), 3.10 (d, 6H), 3.05 (s, 3H), 2.42 (s, 3H), 2.0 (s, 3H).

Workup

filtrationthe resulting solid mass was filtered

Sources & evidence

ORD record: ord-cc47a149fe934c3d9e0d385f982c9295
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907097B2

Reaction notes

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