N-methyl-2-pyrrolidone → HCID 178509526, compound

HRID 496254Notes

Reaction equation

HRID 496254 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.[CH3:26][N:27]1C(=O)CCC1>CCOC(C)=O.[C-]#N.[Zn+2].[C-]#N>[C:26]([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:27]

Participants

5

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 1785190321'-(5-iodo-1H-benzimidazol-2-yl)spiro[isobenzofuran-1,4'-piperidin]-3-one

Product 1

HCID 178509526HCID 178509526, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

Add zinc cyanide (0.016 g, 0.13 mmol) and tetrakistriphenylphosphine palladium(0) (0.018 g, 0.02 mmol) to a solution of 1′-(5-iodo-1H-benzimidazol-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one (0.1 g, 0.22 mmol) in NMP (2 mL). Heat the reaction mixture at 130° C. for 19 hours. After cooling to ambient temperature, dilute the mixture with EtOAc (20 mL), and wash with water (20 mL) and saturated aqueous NaCl (20 mL). Dry the organic portion over Na2SO4, filter and concentrate. Purify by preparative TLC (80% EtOAc-hexane) to obtain 1′-(5-cyano-1H-benzimidazol-2-yl)-spiro[isobenzofuran-1,4′-piperidin]-3-one as a white solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. washwash with water (20 mL) and saturated aqueous NaCl (20 mL)
  3. dry with materialDry the organic portion over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify by preparative TLC (80% EtOAc-hexane)

Sources & evidence

ORD record
ord-e848bb2dc28d4e1bb49747aac602f24a
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Reaction notes

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