Potassium Phosphate, Tribasic → HCID 59368499, compound

HRID 1481472Notes

Reaction equation

HRID 1481472 reaction equation
Br[CH:2]=[C:3]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][N:6]=1)[CH3:4].[O-]P([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O.[CH3:27][N:28]1[CH2:41][CH2:40][C:39]2[C:38]3[CH:37]=[C:36]([CH3:42])[CH:35]=[CH:34][C:33]=3[NH:32][C:31]=2[CH2:30][CH2:29]1>CN(C=O)C.[Cu]I.O>[CH3:27][N:28]1[CH2:41][CH2:40][C:39]2[C:38]3[CH:37]=[C:36]([CH3:42])[CH:35]=[CH:34][C:33]=3[N:32](/[CH:2]=[C:3](/[C:5]3[CH:10]=[CH:9][N:8]=[CH:7][N:6]=3)\[CH3:4])[C:31]=2[CH2:30][CH2:29]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 685600921,2,3,4,5,6-Hexahydro-3,9-dimethylazepino[4,5-b]indoleHCID 86642480HCID 86642480, compound

Product 1

HCID 59368499HCID 59368499, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-(1-bromoprop-1-en-2-yl)pyrimidine (236 mg, 1.2 mmol) was dissolved in DMF (5 mL) and was added K3PO4 (424 mg, 2 mmol) followed by the addition of Copper (I) iodide (19 mg, 0.1 mmol) and L-proline (23 mg, 0.2 mmol). 1,2,3,4,5,6-hexahydro-3,9-dimethylazepino[4,5-b]indole (214 mg, 1 mmol) was added and purged nitrogen for 2 min. Reaction mass was stirred at 85 degree C. for overnight. Water was added and filtered the solid mass under vacuum. Crude was purified on silica gel (100-200 mesh) using 0-10% methanol: dichloromethane as eluent. Yield: 72 mg. 1H NMR (CDCl3, Oxalate salt) δ (ppm): 9.20 (s, 1H), 8.76 (s, 1H), 8.0 (s, 1H), 7.44 (d, 1H), 7.30 (s, 1H), 7.0 (s, 2H), 2.99 (m, 4H), 2.84 (m, 4H), 2.50 (s, 3H), 2.42 (s, 3H), 2.04 (s, 3H).

Workup

  1. custompurged nitrogen for 2 min
  2. customReaction mass
  3. filtrationfiltered the solid mass under vacuum
  4. customCrude was purified on silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-01c5472b166e41148e9e2af9b1f4e93c
Source dataset
uspto-grants-2016_08
Patent number
US09409910B2

Reaction notes

Loading…