Potassium Phosphate, Tribasic → (E)-2,3,8-trimethyl-5-(2-(pyridin-4-yl)prop-1-enyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1400464Notes

Reaction equation

HRID 1400464 reaction equation
[CH3:1][N:2]1[CH:15]([CH3:16])[CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O.Br[CH:34]=[C:35]([C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1)[CH3:36]>CN(C=O)C.[Cu]I>[CH3:1][N:2]1[CH:15]([CH3:16])[CH2:14][C:5]2[N:6](/[CH:34]=[C:35](/[C:37]3[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=3)\[CH3:36])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 666120872,3,8-Trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoleHCID 86642478(E)-4-(1-bromoprop-1-en-2-yl)pyridine

Product 1

HCID 59455258(E)-2,3,8-trimethyl-5-(2-(pyridin-4-yl)prop-1-enyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
140 °C

Procedure

2,3,8-Trimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (107 mg, 0.5 mmol), and potassium phosphate (414 mg, 2 mmol) were mixed in DMF and the suspension was purged with nitrogen. The suspension was heated at 140° C. for 10 min. Copper (I) iodide (9.5 mg, 0.05 mmol) and L-proline (11.5 mg, 0.1 mmol) were added followed by a solution of 4-(1-Bromoprop-1-en-2-yl)pyridine (107.83 mg, 0.55 mmol) in DMF. The contents were purged with nitrogen and heated overnight at 140° C. The contents were cooled to RT and poured into water. The precipitate obtained was filtered, dried and purified by silica gel chromatography (100-200 mesh, neutralized with aqueous ammonia) eluting with 0-4% MeOH-DCM as eluent. The compound was further purified by HPLC. 1H NMR (CDCl3, freebase) δ (ppm): 8.62 (d, 2H), 7.42 (d, 2H), 7.25 (d, 1H), 7.10 (s, 1H), 7.0 (s, 2H), 3.90 (d, 1H), 3.70 (d, 1H), 2.90 (m, 1H), 2.80 (m, 1H), 2.52 (m, 1H), 2.50 (s, 3H), 2.42 (s, 3H), 2.0 (s, 3H), 1.20 (d, 3H).

Workup

  1. customthe suspension was purged with nitrogen
  2. customThe contents were purged with nitrogen
  3. temperatureheated overnight at 140° C
  4. temperatureThe contents were cooled to RT
  5. additionpoured into water
  6. customThe precipitate obtained
  7. filtrationwas filtered
  8. customdried
  9. custompurified by silica gel chromatography (100-200 mesh, neutralized with aqueous ammonia)
  10. washeluting with 0-4% MeOH-DCM as eluent
  11. customThe compound was further purified by HPLC

Sources & evidence

ORD record
ord-e97f64972c464251bcf460c16cb9c161
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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