Potassium Phosphate, Tribasic → HCID 59455093, compound

HRID 1401576Notes

Reaction equation

HRID 1401576 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[S:37][CH:38]=[CH:39][CH:40]=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[S:37][CH:38]=[CH:39][CH:40]=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 85176615HCID 85176615, compound

Product 1

HCID 59455093HCID 59455093, 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 (50 mg, 0.25 mmol) was dissolved in DMF (3 mL), potassium phosphate (106 mg, 0.5 mmol), copper (I) iodide (4.75 mg, 0.025 mmol) and L-proline (5.75 mg, 0.05 mmol) were added. 2-(1-Bromoprop-1-en-2-yl)thiophene (55 mg, 0.275 mmol) was dissolved in DMF (2 mL) and added dropwise to the reaction mixture. The reaction mixture was purged with nitrogen for 2 min. and heated at 85° C. overnight. DMF was evaporated under reduced pressure and water was added to the residue. The product 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: 0.4 mg as the TFA salt. 1H NMR (CDCl3, TFA salt) δ (ppm): 7.30-7.20 (m, 3H), 7.10 (m, 3H), 7.0 (s, 1H), 4.78 (m, 1H), 4.15 (m, 1H), 3.82 (m, 1H), 3.30 (m, 2H), 3.05 (s, 3H), 2.90 (m, 1H), 2.42 (s, 3H), 1.98 (s, 3H).

Workup

  1. additionadded dropwise to the reaction mixture
  2. customThe reaction mixture was purged with nitrogen for 2 min.
  3. customDMF was evaporated under reduced pressure and water
  4. additionwas added to the residue
  5. extractionThe product was extracted with EtOAc (3×25 mL)
  6. washthe organic layer was washed with water (3×25 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-19a5b3a4127c4e57aef3c70a770baf3c
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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