Nitrogen → HCID 59455184, compound

HRID 1400550Notes

Reaction equation

HRID 1400550 reaction equation
Br[CH:2]=[C:3]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)[CH3:4].P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O.N#N.[CH2:29]([N:32]1[CH2:45][CH2:44][C:35]2[NH:36][C:37]3[CH:38]=[CH:39][C:40]([CH3:43])=[CH:41][C:42]=3[C:34]=2[CH2:33]1)[CH:30]=[CH2:31]>CN(C=O)C>[CH2:29]([N:32]1[CH2:45][CH2:44][C:35]2[N:36](/[CH:2]=[C:3](/[C:5]3[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=3)\[CH3:4])[C:37]3[CH:38]=[CH:39][C:40]([CH3:43])=[CH:41][C:42]=3[C:34]=2[CH2:33]1)[CH:30]=[CH2:31]

Participants

7

Reactant 5

HCID 947NitrogenHCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 67312065HCID 67312065, compoundHCID 86642478(E)-4-(1-bromoprop-1-en-2-yl)pyridine

Product 1

HCID 59455184HCID 59455184, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

4-(2-Bromo-1-methyl-vinyl)-pyridine (2.5 g, 13 mmol) and potassium phosphate (4.2 g, 20 mmol) were stirred for 5 min. DMF (20 mL) was added and the solution stirred for 5 min followed by addition of L-proline (230 mg, 2.0 mmol) and cuprous iodide (190 mg, 1.0 mmol). N2 gas was bubbled into the reaction mixture, and 2-Allyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (2.0 g, 10 mmol) was added. The reaction mixture was heated at 120° C. for 16 h. After completion of reaction (as monitored by TLC) the mixture was concentrated under vacuum and diluted with water. The compound was extracted with EtOAc (4×100 mL) and organic layer dried over sodium sulfate, concentrated under vacuum under vacuum. The crude product was purified by column chromatography [Eluent: 2% MeOH in DCM]. 1H NMR (CD3OD, HCl salt) δ (ppm): 8.82 (d, 2H), 8.38 (d, 2H), 7.82 (s, 1H), 7.39 (s, 1H), 7.18 (s, 2H), 6.15 (m, 1H), 5.70 (m, 2H), 4.75 (m, 1H), 4.40 (m, 1H), 4.05 (d, 2H), 3.98 (m, 1H), 3.60 (m, 1H), 3.25 (m, 1H), 3.20 (m, 1H), 2.42 (s, 3H), 2.18 (s, 3H).

Workup

  1. additionwas added
  2. customAfter completion of reaction (as monitored by TLC) the mixture
  3. concentrationwas concentrated under vacuum
  4. additiondiluted with water
  5. extractionThe compound was extracted with EtOAc (4×100 mL) and organic layer
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum under vacuum
  8. customThe crude product was purified by column chromatography [Eluent: 2% MeOH in DCM]

Sources & evidence

ORD record
ord-98db990845944ee89359706eb8cfbcb0
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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