Sodium Carbonate → 2-[4-(10-[1,1';3',1'']Terphenyl-5'-yl-anthracen-9-yl)-phenyl]-imidazo [1,2-a] pyridine

HRID 251765Notes

Reaction equation

HRID 251765 reaction equation
Br[C:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[N:23]=[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]4[CH:30]=3)=[CH:18][CH:17]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[C:31]1([C:37]2[CH:42]=[C:41](B(O)O)[CH:40]=[C:39]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH:38]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.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>[C:31]1([C:37]2[CH:42]=[C:41]([C:2]3[C:3]4[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=4)[C:9]([C:16]4[CH:21]=[CH:20][C:19]([C:22]5[N:23]=[C:24]6[CH:29]=[CH:28][CH:27]=[CH:26][N:25]6[CH:30]=5)=[CH:18][CH:17]=4)=[C:10]4[C:15]=3[CH:14]=[CH:13][CH:12]=[CH:11]4)[CH:40]=[C:39]([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[CH:38]=2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 14739363(1~1~,2~1~:2~3~,3~1~-Terphenyl)-2~5~-ylboronic acidHCID 859091942-[4-(10-Bromo-9-anthracenyl)phenyl]imidazo[1,2-a]pyridine

Product 1

HCID 866063802-[4-(10-[1,1';3',1'']Terphenyl-5'-yl-anthracen-9-yl)-phenyl]-imidazo [1,2-a] pyridineYield 72.9%

Reagents, catalysts & solvents 2

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

Procedure

Two point five grams (5.5 mmol) of 2-[4-(10-bromo-anthracen-9-yl)-phenyl]-imidazo [1,2-a] pyridine, 1.6 g (5.8 mmol) of [1,1′;3′,1″] terphenyl-5′-boronic acid and 0.13 g of tetrakis (triphenylphosphine) palladium were dissolved into 20 milliliter of 1,2-dimethoxyethane, and adding 9 milliliter of 2.0M sodium carbonate aqueous solution, the resultant suspension was refluxed under heating for 8 hours. After completion of the reaction, separation with filtration was carried out and resultant crystals were washed with water and methanol, thereby obtaining 2.4 g of yellowish white solids (yield: 71%). 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=598 for molecular weight of 598.24.

Workup

  1. temperatureunder heating for 8 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-e4d5c34a344b4461a8a1ced60dc758ba
Source dataset
uspto-grants-2011_01
Patent number
US07867629B2

Reaction notes

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