Potassium Phosphate, Tribasic → HCID 59454948, compound

HRID 1400519Notes

Reaction equation

HRID 1400519 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH2:15][CH2:16][OH:17])[CH2:14][C:5]=3[C:4]=2[CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O.Br[CH:35]=[C:36]([C:38]1[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=1)[CH3:37]>CN(C=O)C.[Cu]I>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7](/[CH:35]=[C:36](/[C:38]3[CH:43]=[CH:42][N:41]=[CH:40][CH:39]=3)\[CH3:37])[C:6]3[CH2:11][CH2:12][N:13]([CH2:15][CH2:16][OH:17])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 67311112HCID 67311112, compoundHCID 86642478(E)-4-(1-bromoprop-1-en-2-yl)pyridine

Product 1

HCID 59454948HCID 59454948, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
85 °C

Procedure

2-(3,4-dihydro-8-methyl-1H-pyrido[4,3-b]indol-2(5H)-yl)ethanol (232 mg, 1 mmol) was dissolved in DMF (3 mL) and potassium phosphate (424 mg, 2 mmol), copper(I) iodide (19 mg, 0.1 mmol) and L-proline (23 mg, 0.2 mmol) was added in to it. 4-(1-bromoprop-1-en-2-yl)pyridine (294 mg, 1.5 mmol) was dissolved in DMF (2 mL) and added dropwise. Nitrogen was purged for 2 min. and the reaction mixture was heated at 85° C. overnight (prolonged heating was required in some cases). DMF was evaporated and water was added. The precipitate obtained was filtered and purified by silica gel chromatography (100-200 mesh) using 0-8% MeOH:DCM as eluent. The compound was further purified through reverse phase purification. Yield: 115 mg. 1H NMR (CD3OD, oxalate salt) δ (ppm): 8.70 (d, 2H), 7.68 (d, 2H), 7.38 (m, 2H), 7.10 (m, 2H), 4.60 (m, 2H), 4.0 (m, 2H), 3.78 (m, 2H), 3.50 (m, 2H), 3.15 (m, 2H), 2.42 (s, 3H), 2.05 (s, 3H).

Workup

  1. additionadded dropwise
  2. customNitrogen was purged for 2 min.
  3. temperatureprolonged heating
  4. customDMF was evaporated
  5. additionwater was added
  6. customThe precipitate obtained
  7. filtrationwas filtered
  8. custompurified by silica gel chromatography (100-200 mesh)
  9. customThe compound was further purified through reverse phase purification

Sources & evidence

ORD record
ord-d4122fa9929e4261abed2f4436117c2d
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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