Potassium Phosphate, Tribasic → HCID 86644777, compound

HRID 1401665Notes

Reaction equation

BrC=C([C:5]1[CH:15]=[CH:14][C:8]([C:9]([N:11]([CH3:13])[CH3:12])=[O:10])=[CH:7][CH:6]=1)C.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]([C:8]3([CH:7]=[CH:6][CH:5]=[CH:15][CH2:14]3)[C:9]([N:11]([CH3:12])[CH3:13])=[O:10])[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 (5 mL) and 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 and the mixture purged with nitrogen for 2 min. The reaction mixture was stirred at 85° C. overnight. Water was added and the solid mass was filtered under vacuum. The crude compound was purified on silica gel (100-200 mesh) using 0-7% MeOH:DCM as eluent. Yield: 60 mg. 1H NMR (CD3OD, oxalate salt) δ (ppm): 7.30 (m, 2H), 7.20 (s, 2H), 7.10 (d, 1H), 6.95 (d, 1H), 6.86 (s, 1H), 6.80 (s, 1H), 4.58 (m, 1H), 4.30 (m, 1H), 3.60 (m, 1H), 3.10 (m, 1H), 3.0 (s, 3H), 2.92 (s, 3H), 2.80 (m, 2H), 2.50 (s, 3H), 2.39 (s, 3H), 2.36 (s, 3H),

Workup

customthe mixture purged with nitrogen for 2 min
additionWater was added
filtrationthe solid mass was filtered under vacuum
customThe crude compound was purified on silica gel (100-200 mesh)

Sources & evidence

ORD record: ord-f5a4428b843e452b891bf414bb3a2984
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907097B2

Reaction notes

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