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

HRID 413238Notes

Reaction equation

HRID 413238 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-4c17649609a4440488c2c7c52dd112cd
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Reaction notes

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