Potassium Phosphate, Tribasic → HCID 59454935, compound

HRID 1401545Notes

Reaction equation

HRID 1401545 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.Br[CH:17]=[C:18]([C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)[CH:19]([CH3:21])[CH3:20].P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O>CN(C=O)C.[Cu]I>[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[N:6](/[CH:17]=[C:18](\[C:22]3[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=3)/[CH:19]([CH3:21])[CH3:20])[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 86644759HCID 86644759, compound

Product 1

HCID 59454935HCID 59454935, compound

Reagents, catalysts & solvents 2

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

Procedure

2,3,4,5-Tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole (0.08 g, 0.4 mmol), 4-(1-bromo-3-methylbut-1-en-2-yl)pyridine (0.1 g, 0.44 mmol), potassium phosphate (0.169 g, 0.797 mmol), L-proline (0.013 g, 0.113 mmol), and copper (I) iodide (0.015 g, 0.079 mmol) were mixed in DMF (5 mL) and purged with nitrogen. The contents were cooled to RT and poured into water. The precipitate obtained was filtered, dried and purified by HPLC. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.50 (d, 2H), 7.60 (d, 2H), 7.20 (s, 1H), 7.10 (d, 1H), 6.95 (d, 2H), 4.60 (m, 1H), 4.30 (m, 1H), 3.80 (m, 1H), 3.50 (m, 1H), 3.10 (m, 1H), 3.05 (m, 5H), 2.38 (s, 3H), 1.38 (d, 6H).

Workup

  1. custompurged with nitrogen
  2. additionpoured into water
  3. customThe precipitate obtained
  4. filtrationwas filtered
  5. customdried
  6. custompurified by HPLC

Sources & evidence

ORD record
ord-4fb2902b08b74c4a879b296e0553830f
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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