Potassium Phosphate, Tribasic → HCID 59454948, compound

HRID 1401599Notes

Reaction equation

HRID 1401599 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). potassium phosphate (424 mg, 2 mmol), copper (I) iodide (19 mg, 0.1 mmol) and L-proline (23 mg, 0.2 mmol) were added. 4-(1-bromoprop-1-en-2-yl)pyridine (294 mg, 1.5 mmol) dissolved in DMF (2 mL) was added dropwise to the reaction mixture. Nitrogen was purged for 2 min in the reaction mixture which was heated at 85° C. overnight (prolonged heating was required in some cases). DMF was evaporated and water added to the reaction mixture. 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. additionwas added dropwise to the reaction mixture
  2. customNitrogen was purged for 2 min in the reaction mixture which
  3. temperatureprolonged heating
  4. customDMF was evaporated
  5. additionwater added to the reaction mixture
  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-803d3903f9454e888bbd9c52e9c62785
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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