Sodium Carbonate → HCID 178519028, compound

HRID 496252Notes

Reaction equation

HRID 496252 reaction equation
I[C:2]1[CH:25]=[CH:24][C:5]2[NH:6][C:7]([N:9]3[CH2:14][CH2:13][C:12]4([C:22]5[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=5)[C:16](=[O:23])[O:15]4)[CH2:11][CH2:10]3)=[N:8][C:4]=2[CH:3]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[C:28](B(O)O)[CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[N:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:2]2[CH:25]=[CH:24][C:5]3[NH:6][C:7]([N:9]4[CH2:14][CH2:13][C:12]5([C:22]6[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=6)[C:16](=[O:23])[O:15]5)[CH2:11][CH2:10]4)=[N:8][C:4]=3[CH:3]=2)[CH:27]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 1785190321'-(5-iodo-1H-benzimidazol-2-yl)spiro[isobenzofuran-1,4'-piperidin]-3-one

Product 1

HCID 178519028HCID 178519028, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Add tetrakistriphenylphosphine palladium(0)(0.01 g, 0.01 mmol) to 1′-(5-iodo-1H-benzimidazol-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one (0.10 g, 0.22 mmol) in ethylene glycol dimethyl ether (2 mL). To this solution, add pyridine-3-boronic acid (0.06 g, 0.45 mmol) and aqueous sodium carbonate (1M, 1 mL) and heat the reaction at 80° C. for 2 hours. Extract the product with EtOAc (20 mL). Wash the combined extracts with brine (20 mL), dry over sodium sulfate, and concentrate in vacuo. Purify by flash column chromatography (5% MeOH—CH2Cl2) to obtain 1′-(5-pyridin-3-yl-1H-benzimidazol-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one as a white solid.

Workup

  1. temperatureheat
  2. customthe reaction at 80° C. for 2 hours
  3. extractionExtract the product with EtOAc (20 mL)
  4. washWash the combined extracts with brine (20 mL)
  5. dry with materialdry over sodium sulfate
  6. concentrationconcentrate in vacuo
  7. customPurify by flash column chromatography (5% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-1b914407c4db44b4937785bbf8225769
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Reaction notes

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