Sodium Carbonate → HCID 178519028, compound

HRID 413236Notes

Reaction equation

HRID 413236 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)(0.1 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-1dcb3251b716472b8a8fed4bfe71a288
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Reaction notes

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