Sodium Carbonate → 2-(4'-formylbipheny-4-yl)-1H-benzimidazole-4-carboxamide

HRID 736691Notes

Reaction equation

HRID 736691 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[C:16]([C:17]([NH2:19])=[O:18])[C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[CH:20]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)=[O:21].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:20]([C:22]1[CH:27]=[CH:26][C:25]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[NH:12][C:11]4[CH:13]=[CH:14][CH:15]=[C:16]([C:17]([NH2:19])=[O:18])[C:10]=4[N:9]=3)=[CH:4][CH:3]=2)=[CH:24][CH:23]=1)=[O:21]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 445423652-(4-bromophenyl)-1H-benzimidazole-4-carboxamide

Product 1

HCID 875005162-(4'-formylbipheny-4-yl)-1H-benzimidazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

A solution of EXAMPLE 3A (1.18 g, 3.8 mmol) and 4-formylphenylboronic acid (0.57 g, 3.8 mmol) in dioxane (15 mL) was treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium (0.32 g, 0.4 mmol) and sodium carbonate (1.8 g, 17 mmol). The mixture was heated at 95° C. for 24 hours, then cooled and filtered. The filtrate was concentrated to provide the crude product, which was used without further purification. MS (ESI) m/e 342 (M+H)+.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c3eb51b6e1c644a9a75c341c8f7ce0b4
Source dataset
uspto-grants-2009_09
Patent number
US07595406B2

Reaction notes

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