Potassium Phosphate, Tribasic → HCID 59454892, compound

HRID 1401575Notes

Reaction equation

HRID 1401575 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:37]=[N:38][CH:39]=[N:40][CH:41]=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:37]=[N:38][CH:39]=[N:40][CH:41]=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 86644761HCID 86644761, compound

Product 1

HCID 59454892HCID 59454892, 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 mg, 1 mmol), copper(I) iodide (9 mg, 0.05 mmol) and L-proline (11 mg, 0.1 mmol) was added. 5-(1-Bromoprop-1-en-2-yl)pyrimidine (98 mg, 0.5 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 under reduced pressure and water was added to the residue obtained. Compound was extracted with EtOAc (3×25 mL), the organic layer was washed with water (3×25 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by HPLC. Yield: 7 mg as the TFA salt. 1H NMR (CD3OD, TFA salt) δ (ppm): 9.18 (s, 1H), 9.08 (s, 2H), 7.35 (s, 1H), 7.24 (s, 1H), 7.18 (d, 1H), 7.10 (d, 1H), 4.78 (m, 1H), 3.30 (m, 1H), 3.85 (m, 1H), 3.60 (m, 1H), 3.20 (m, 2H), 3.10 (s, 3H), 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 under reduced pressure and water
  5. additionwas added to the residue
  6. customobtained
  7. extractionCompound was extracted with EtOAc (3×25 mL)
  8. washthe organic layer was washed with water (3×25 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-bf75090683454d49bec2dc4ad1c55a8b
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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