Dimethylformamide → HCID 25027771, compound

HRID 2189135Notes

Reaction equation

HRID 2189135 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([O:16][CH2:17][C:4]=2[CH:3]=1)[C:15]1[N:11]([CH:12]=[N:13][CH:14]=1)[CH2:10][CH2:9]3.[CH3:18][N:19](C)C=O>[C-]#N.[Zn+2].[C-]#N.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH:14]1[N:13]=[CH:12][N:11]2[CH2:10][CH2:9][C:8]3([C:5]4[CH:6]=[CH:7][C:2]([C:18]#[N:19])=[CH:3][C:4]=4[CH2:17][O:16]3)[C:15]=12

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 68614230HCID 68614230, compound

Product 1

HCID 25027771HCID 25027771, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
120 °C

Procedure

To a degassed solution of 31.2 mmol of 5-bromo-5′,6′-dihydro-3H-spiro[2-benzofuran-1,7′-pyrrolo[1,2-c]imidazole]] in 90 ml of N,N-dimethylformamide are added 62.4 mmol of zinc(II) cyanide and 1.25 mmol of [1,1′-bis(diphenylphosphino)ferrocene]-dichloro palladium. The mixture is heated at 120° C. for 16 h. The mixture is poured into ice water and extracted with ethyl acetate. The combined organics are dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (SiO2 60 F) followed by crystallization from diethyl ether to afford the title compound as a beige solid. Rf=0.33 (dichloromethane-2M ammonia in ethanol 95:5); Rt=4.62 (gradient II).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organics are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by flash chromatography (SiO2 60 F)
  6. customfollowed by crystallization from diethyl ether

Sources & evidence

ORD record
ord-4f1a941ad8704d0a80da6dfcb50b556d
Source dataset
uspto-grants-2012_12
Patent number
US08324235B2

Reaction notes

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