Potassium Carbonate → HCID 58162331, compound

HRID 1097132Notes

Reaction equation

HRID 1097132 reaction equation
Br[C:2]1[C:15]2[N:14]3[CH:16]=[CH:17][N:18]=[C:13]3[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:19]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2].COCCOC>[CH:19]([C:22]1[CH:27]=[CH:26][C:25]([C:2]2[C:15]3[N:14]4[CH:16]=[CH:17][N:18]=[C:13]4[C:12]4[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=4[C:6]=3[CH:5]=[CH:4][CH:3]=2)=[CH:24][CH:23]=1)([CH3:21])[CH3:20]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27734804-Isopropylphenylboronic acidHCID 66813586HCID 66813586, compound

Product 1

HCID 58162331HCID 58162331, compoundYield 77.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A three neck 1 L round bottom flask was charged with 5-bromo-imidazo[1,2-f]phenanthridine (4.55 g, 15.31 mmole), 4-isopropylphenylboronic acid (3.59 g, 21.89 mmole), potassium carbonate (2N aqueous soln., 27 ml), Pd(OAc)2 (223 mg, 0.99 mmole), triphenylphosphine (1.044 g, 3.98 mmole) and 100 ml of 1,2-dimethoxyethane. The reaction mixture was heated to 80° C. under nitrogen for 17 hrs. The reaction mixture was diluted with methylene chloride and washed by brine. The organic fractions were combined, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude mixture was purified by chromography on silica gel using hexane/ethyl acetate (80/20) to obtain pure 5-(4-isopropylphenyl)-imidazo[1,2-f]phenanthridine (4 g, 77%).

Workup

  1. washwashed by brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude mixture was purified by chromography on silica gel

Sources & evidence

ORD record
ord-2a27ecf88dd94b86a51fd0c30d998353
Source dataset
uspto-grants-2012_03
Patent number
US08142909B2

Reaction notes

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