L-Proline → HCID 59455151, compound

HRID 1401550Notes

Reaction equation

HRID 1401550 reaction equation
[CH2:1]([N:3]1[CH2:16][CH2:15][CH:6]2[NH:7][C:8]3[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][C:13]=3[CH:5]2[CH2:4]1)[CH3:2].N1CCC[C@H]1C(O)=O.Br[CH:26]=[C:27]([C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)[CH3:28]>CN(C=O)C.[Cu]I>[CH2:1]([N:3]1[CH2:16][CH2:15][C:6]2[N:7](/[CH:26]=[C:27](/[C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)\[CH3:28])[C:8]3[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][C:13]=3[C:5]=2[CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 145742L-ProlineHCID 12527880HCID 12527880, compoundHCID 86642478(E)-4-(1-bromoprop-1-en-2-yl)pyridine

Product 1

HCID 59455151HCID 59455151, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

2-Ethyl-8-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole (150 mg, 0.69 mmol) potassium phosphate (292.5 mg, 1.382 mmol), Copper (I) iodide (13.11 mg, 0.069 mmol) and L-proline (15.8 mg, 0.138 mmol) were mixed in DMF and the purged with nitrogen. The contents were heated at 80° C. for 10 min. 4-(1-Bromoprop-1-en-2-yl)pyridine (208 mg, 1.04 mmol) was added, the reaction mixture was purged 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 HPLC. 1H NMR (CD3OD, freebase) δ (ppm): 8.58 (d, 2H), 7.70 (d, 2H), 7.35 (s, 1H), 7.30 (s, 1H), 7.05 (m, 2H), 3.95 (s, 2H), 3.10 (q, 2H), 2.95 (m, 4H), 2.42 (s, 3H), 2.00 (s, 3H), 1.30 (t, 3H).

Workup

  1. customthe purged with nitrogen
  2. customthe reaction mixture was purged 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 HPLC

Sources & evidence

ORD record
ord-3401ee90bac1445ebe1ec3c5da9983c6
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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