Potassium Phosphate, Tribasic → HCID 59454987, compound

HRID 1401718Notes

Reaction equation

HRID 1401718 reaction equation
[Cl:1][C:2]1[C:10]2[NH:9][C:8]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.N1CCC[C@H]1C(O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[CH:33]=[C:34]([C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=1)[CH3:35]>CN(C=O)C.[Cu]I>[Cl:1][C:2]1[C:10]2[N:9]([CH2:35][C:34]([C:36]3[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=3)=[CH2:33])[C:8]3[CH2:11][CH2:12][N:13]([CH3:15])[CH2:14][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 50915806-Chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleHCID 86644757(1-Bromoprop-1-en-2-yl)-4-fluorobenzene

Product 1

HCID 59454987HCID 59454987, compound

Reagents, catalysts & solvents 2

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

Procedure

6-Chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (200 mg, 0.909 mmol) was dissolved in DMF (4 mL). Copper (I) iodide (14 mg, 0.089 mmol), L-proline (20 mg, 0.173 mmol) and K3PO4 (380 mg, 1.79 mmol) were added and the reaction mixture was stirred for 10 min at RT. 1-(1-Bromoprop-1-en-2-yl)-4-fluorobenzene (250 mg, 1.17 mmol) was added dropwise and the reaction mixture was purged with nitrogen. The reaction mixture was heated at 85° C. overnight (prolonged heating in some cases was required). DMF was evaporated under reduced pressure, the residue was diluted with water, and the solid was filtered. The solid material was purified by silica gel chromatography (100-200 mesh) eluting with 0-5% MeOH-DCM. 1H NMR (CD3OD, oxalate salt) δ (ppm): 7.60 (m, 2H), 7.45 (d, 1H), 7.20-7.05 (m, 4H), 5.50 (s, 2H), 5.30 (s, 1H), 4.55 (m, 2H), 4.05 (s, 1H), 3.70 (m, 2H), 3.18 (m, 2H), 3.10 (s, 3H).

Workup

  1. customthe reaction mixture was purged with nitrogen
  2. temperatureThe reaction mixture was heated at 85° C. overnight (
  3. temperatureprolonged heating in some cases
  4. customDMF was evaporated under reduced pressure
  5. additionthe residue was diluted with water
  6. filtrationthe solid was filtered
  7. customThe solid material was purified by silica gel chromatography (100-200 mesh)
  8. washeluting with 0-5% MeOH-DCM

Sources & evidence

ORD record
ord-bda1844b36184cbaa4ee91466dfdca01
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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