Potassium Phosphate, Tribasic → HCID 59455240, compound

HRID 1401551Notes

Reaction equation

HRID 1401551 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][C:9]2[NH:8][CH:7]3[CH2:12][CH2:13][N:14]([CH3:16])[CH2:15][CH:6]3[C:5]=2[CH:4]=1)[CH3:2].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>[CH2:1]([C:3]1[CH:11]=[CH:10][C:9]2[N:8](/[CH:34]=[C:35](/[C:37]3[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=3)\[CH3:36])[C:7]3[CH2:12][CH2:13][N:14]([CH3:16])[CH2:15][C:6]=3[C:5]=2[CH:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 67309867HCID 67309867, compoundHCID 86642478(E)-4-(1-bromoprop-1-en-2-yl)pyridine

Product 1

HCID 59455240HCID 59455240, compound

Reagents, catalysts & solvents 2

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

Procedure

8-Ethyl-2-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole (200 mg, 0.9345 mmol), potassium phosphate (396 mg, 1.8 mmol), copper (I) iodide (21 mg, 0.18 mmol), L-proline (17 mg, 0.09345 mmol) and 4-(1-bromoprop-1-en-2-yl)pyridine (277 mg, 1.40 mmol) were mixed in DMF and the reaction mixture was purged with nitrogen. The contents were cooled to RT and poured into water. The precipitate obtained was filtered, dried and purified by HPLC. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.58 (d, 2H), 7.70 (d, 2H), 7.36 (s, 1H), 7.22 (s, 1H), 7.05 (m, 2H), 3.75 (s, 2H), 2.95 (m, 2H), 2.85 (m, 2H), 2.70 (q, 2H), 2.38 (s, 3H), 2.00 (s, 3H), 1.25 (t, 3H).

Workup

  1. customthe reaction mixture was purged with nitrogen
  2. additionpoured into water
  3. customThe precipitate obtained
  4. filtrationwas filtered
  5. customdried
  6. custompurified by HPLC

Sources & evidence

ORD record
ord-7e66fe0c3eda476cbdd1c23e6ea5d66b
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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