Sodium Carbonate → 2-[4-(10-Naphthalen-2-yl-anthracen-9-yl)-phenyl]-6-phenyl-imidazo [1,2-a] pyridine

HRID 251776Notes

Reaction equation

HRID 251776 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:12][N:11]3[CH:22]=2)=[CH:4][CH:3]=1.[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[C:33]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:40](B(O)O)=[C:39]2[C:34]=1[CH:35]=[CH:36][CH:37]=[CH:38]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:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[C:33]1[C:34]2[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:40]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:9]=[C:10]4[CH:15]=[CH:14][C:13]([C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=5)=[CH:12][N:11]4[CH:22]=3)=[CH:4][CH:3]=2)=[C:41]2[C:46]=1[CH:45]=[CH:44][CH:43]=[CH:42]2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2308855610-(2-Naphthyl)anthracene-9-boronic AcidHCID 230885602-(4-Bromo-phenyl)-6-phenyl-imidazo [1,2-a] pyridine

Product 1

HCID 584353672-[4-(10-Naphthalen-2-yl-anthracen-9-yl)-phenyl]-6-phenyl-imidazo [1,2-a] pyridineYield 77.8%

Reagents, catalysts & solvents 2

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

Procedure

Dissolving 4.0 g (11 mmol) of 2-(4-bromo-phenyl)-6-phenyl-imidazo [1,2-a] pyridine, 4.0 g (11 mmol) of 10-naphthalen-2-yl-anthracene-9-boronic acid and 0.27 g of tetrakis (triphenylphosphine) palladium into 40 milliliter of 1,2-dimethoxyethane, adding 18 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 crystals were washed with water and methanol, thereby obtaining 4.9 g of yellowish white solids (yield: 76%). As a result of mass spectrum (MS) analysis, it was recognized that m/e=572 for molecular weight of 572.23 and the yellowish white solids were identified as the aimed substance.

Workup

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

Sources & evidence

ORD record
ord-382643f4d0394332b2d4cddaf407e554
Source dataset
uspto-grants-2011_01
Patent number
US07867629B2

Reaction notes

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