Potassium Phosphate, Tribasic → HCID 59455099, compound

HRID 1400540Notes

Reaction equation

HRID 1400540 reaction equation
[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O.Br[CH:33]=[C:34]([C:36]1[CH:40]=[CH:39][S:38][CH:37]=1)[CH3:35]>CN(C=O)C.[Cu]I>[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[N:6](/[CH:33]=[C:34](/[C:36]3[CH:40]=[CH:39][S:38][CH:37]=3)\[CH3:35])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 2092911H-Pyrido[4,3-b]indole, 2,3,4,5-tetrahydro-2,8-dimethyl-HCID 86644766HCID 86644766, compound

Product 1

HCID 59455099HCID 59455099, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
85 °C

Procedure

2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole (100 mg, 0.5 mmol) was dissolved in DMF (3 mL). potassium phosphate (212.4 mg, 1 mmol), Copper (I) iodide (9.5 mg, 0.05 mmol) and L-proline (11.51 mg, 0.1 mmol) were added. 3-(1-bromoprop-1-en-2-yl)thiophene (121.8 mg, 0.6 mmol) dissolved in DMF (2 mL) was added dropwise to the reaction mixture. Nitrogen was purged for 2 min and the reaction mixture heated at 85° C. overnight (prolonged heating required some cases). DMF was evaporated and water added to the reaction mixture. The precipitate obtained was filtered and purified through silica gel chromatography (100-200 mesh) using 0-3% MeOH:DCM as eluent. The compound was further purified through reverse phase purification. Yield: 80 mg. 1H NMR (CD3OD, oxalate salt) δ (ppm): 7.60 (s, 1H), 7.50 (m, 2H), 7.30 (s, 1H), 7.18 (s, 1H), 7.10 (m, 2H), 4.55 (m, 2H), 3.70 (m, 2H), 3.10 (m, 5H), 2.42 (s, 3H), 1.95 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-4ed01b5dceaf48839a05c68221832675
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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