Dimethylformamide → HCID 67367542, compound

HRID 1753141Notes

Reaction equation

HRID 1753141 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:8]3[CH2:11][CH2:12][NH:13][C:7]3([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH2:6][N:5]2[CH:22]=1.[CH3:23][N:24](C=O)C>[C-]#N.[Zn+2].[C-]#N>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:7]23[NH:13][CH2:12][CH2:11][N:8]2[C:9](=[O:10])[C:4]2[N:5]([CH:22]=[C:2]([C:23]#[N:24])[CH:3]=2)[CH2:6]3)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 58406353HCID 58406353, compound

Product 1

HCID 67367542HCID 67367542, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Conditions

Temperature
160 °C

Procedure

7-bromo-10a-(4-methoxyphenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (100 mg, 0.28 mmol), zinc cyanide (50 mg, 0.42 mmol) and palladium(0) tetrakistriphenylphosphine (32 mg, 0.03 mmol) were suspended in dry DMF (3 mL) in a microwave vial flushed with argon. The mixture was heated in the microwave reactor at 160° C. for 20 minutes. A saturated aqueous solution of NaHCO3 (50 mL) was added and the mixture extracted with CH2Cl2 containing 20% of isopropyl alcohol. The organic layers were dried (MgSO4), filtrated and concentrated in vacuo. The resulting residue was purified by flash chromatography (Biotage SP4, 12 g cartridge, gradient 0-5% methanol in CH2Cl2) to give 10a-(4-methoxyphenyl)-5-oxo-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazine-7-carbonitrile (50 mg, yield 58%) ESI-MI m/z [M+H]+ 308.9. Used in the next step without further purification.

Workup

  1. customvial flushed with argon
  2. additionA saturated aqueous solution of NaHCO3 (50 mL) was added
  3. extractionthe mixture extracted with CH2Cl2 containing 20% of isopropyl alcohol
  4. dry with materialThe organic layers were dried (MgSO4)
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by flash chromatography (Biotage SP4, 12 g cartridge, gradient 0-5% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-8e1b34e71d0e4b7b9cb30bac2e2e5b07
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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