Sodium Carbonate → 6-(10-Naphthalen-2-yl-anthracen-9-yl)-2-phenyl-imidazo [1,2-a] pyridine

HRID 251773Notes

Reaction equation

HRID 251773 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[C:27]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34](B(O)O)=[C:33]2[C:28]=1[CH:29]=[CH:30][CH:31]=[CH:32]2.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[C:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:34]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([CH:8]=[C:9]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[N:10]=3)[CH:7]=2)=[C:35]2[C:40]=1[CH:39]=[CH:38][CH:37]=[CH:36]2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6234306-Bromo-2-phenylimidazo[1,2-a]pyridineHCID 2308855610-(2-Naphthyl)anthracene-9-boronic Acid

Product 1

HCID 230885636-(10-Naphthalen-2-yl-anthracen-9-yl)-2-phenyl-imidazo [1,2-a] pyridineYield 75%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Dissolving 2.0 g (7.3 mmol) of 6-bromo-2-phenyl-imidazo [1,2-a] pyridine, 2.5 g (11 mmol) of 10-naphthalen-2-yl-anthracene-9-boronic acid and 0.17 g of tetrakis (triphenylphosphine) palladium into 20 milliliter of 1,2-dimethoxyethane, adding 11 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 7 hours. After completion of the reaction, separation with filtration was carried out and resultant crystal were washed with water and methanol, thereby obtaining 2.7 g of yellowish white solids (yield: 75%). As a result of mass spectrum (MS) analysis, the yellowish white solids were identified as the aimed substance, and it was recognized that m/e=496 for molecular weight of 496.19.

Workup

  1. temperatureunder heating for 7 hours
  2. customAfter completion of the reaction, separation
  3. filtrationwith filtration
  4. washresultant crystal were washed with water and methanol

Sources & evidence

ORD record
ord-3b79997b904b476a9fee74998a92c3b9
Source dataset
uspto-grants-2011_01
Patent number
US07867629B2

Reaction notes

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