Sodium Bicarbonate → HCID 86754226, compound

HRID 581904Notes

Reaction equation

HRID 581904 reaction equation
[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:20]=[CH:19][C:8]2[N:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14](Br)[CH:13]=3)[CH:10]=[N:11][C:7]=2[CH:6]=1.[O:21]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22]1.C(=O)(O)[O-].[Na+]>O.C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][N:3]=[CH:4][C:5]1[CH:20]=[CH:19][C:8]2[N:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:23]4[CH:24]=[CH:25][O:21][CH:22]=4)[CH:13]=3)[CH:10]=[N:11][C:7]=2[CH:6]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734358Furan-3-boronic acidHCID 54320977HCID 54320977, compound

Product 1

HCID 86754226HCID 86754226, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(3-Bromophenyl)-5-formylbenzimidazole O-methyloxime (29a) from Example 8 (0.7 g, 2.1 mmol), 3-furanylboronic acid (0.26 g, 2.34 mmol), sodium bicarbonate (0.89 g, 10.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (50 mg) in a mixture of water (5 ml) and dimethoxyethane (10 ml) is stirred at 80° C. under nitrogen over night. After cooling water is added and the mixture is extracted with ethyl acetate. The extract is dried over sodium sulfate and concentrated under reduced pressure. The residue is eluted through silica gel with a mixture of ethyl acetate and petroleum ether (1:1). The pure fractions are evaporated to dryness. Trituration with petroleum ether affords a white, crystalline product. Yield: 0.42 g (63%). Mp 147-148° C.

Workup

  1. additionis added
  2. extractionthe mixture is extracted with ethyl acetate
  3. dry with materialThe extract is dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe residue is eluted through silica gel with a mixture of ethyl acetate and petroleum ether (1:1)
  6. customThe pure fractions are evaporated to dryness
  7. customTrituration with petroleum ether affords a white, crystalline product

Sources & evidence

ORD record
ord-f5abe4acae0248b68f4a3879c0433d68
Source dataset
uspto-grants-1999_07
Patent number
US05922725

Reaction notes

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