Nitrogen → HCID 59455266, compound

HRID 1401625Notes

Reaction equation

HRID 1401625 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:22].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)C=C>CN(C=O)C>[CH3:43][C:40]1[CH:39]=[CH:38][C:37]2[N:36](/[CH:2]=[C:3](/[C:5]3[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=3)\[CH3:4])[C:35]3[CH2:44][CH2:45][N:32]([CH:29]=[O:22])[CH2:33][C:34]=3[C:42]=2[CH:41]=1

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 59455266HCID 59455266, 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 contents stirred for 5 min. L-proline (230 mg, 2.0 mmol) and cuprous iodide (190 mg, 1.0 mmol) were added to the reaction mixture and N2 bubbled into the reaction mixture. 2-Allyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (2.0 g, 10 mmol) was added and the contents heated at 120° C. for 16 h. After completion of reaction (as monitored by TLC) the reaction mixture was concentrated under vacuum and diluted with water. The desired compound was extracted with EtOAc (4×100 mL). The organic layer was dried over sodium sulfate and concentrated under vacuum to obtain the crude product, which was purified by column chromatography [Eluent: 2% MeOH in DCM]. 1H NMR (DMSO, free base) δ (ppm): 8.60 (d, 2H), 8.20 (s, 1H), 7.64 (d, 2H), 7.42 (s, 1H), 7.32 (s, 1H), 7.10 (d, 1H), 4.60 (d, 2H), 3.80 (m, 2H), 2.80 (m, 2H), 2.41 (s, 3H), 1.96 (s, 3H).

Workup

  1. custombubbled into the reaction mixture
  2. customAfter completion of reaction (as monitored by TLC) the reaction mixture
  3. concentrationwas concentrated under vacuum
  4. additiondiluted with water
  5. extractionThe desired compound was extracted with EtOAc (4×100 mL)
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7a3bfbad0f0545799ad85bc2c8acccce
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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