Potassium Carbonate → HCID 58162331, compound

HRID 338182Notes

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

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 chromagraphy on silica gel using hexane/ethyl acetate (80/20) to obtain pure 5-(4-isopropylphenyl)-imidazo[1,2-f]phenanthridine (4 g, 77%).

Workup

washwashed by brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude mixture was purified by chromagraphy on silica gel

Sources & evidence

ORD record: ord-bd259814a81443769a49673d29afaf8b
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889864B2

Reaction notes

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