Diiodomethane → HCID 86720053, compound

HRID 510120Notes

Reaction equation

HRID 510120 reaction equation
I[CH2:2][I:3].N(OCCC(C)C)=O.NC1[N:21]=[C:20]([C:22]2[C:30]3[C:25](=[N:26][CH:27]=[CH:28][CH:29]=3)[N:24]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[F:38])[N:23]=2)[N:19]=[C:18]2[C:14]=1[N:15]([CH:40]([CH3:42])[CH3:41])[C:16](=[O:39])[NH:17]2>>[F:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[CH2:31][N:24]1[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:30]2[C:22]([C:20]2[N:19]=[C:18]3[C:14]([N:15]([CH:40]([CH3:42])[CH3:41])[C:16](=[O:39])[NH:17]3)=[C:2]([I:3])[N:21]=2)=[N:23]1

Participants

4

Reactant 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 66614271HCID 66614271, compound

Product 1

HCID 86720053HCID 86720053, compoundYield 57.7%

Conditions

Temperature
85 °C

Procedure

To a mixture of 2.59 ml (32.20 mmol) of diiodomethane and 2.78 ml (20.61 mmol) of isoamyl nitrite were added 539 mg (approx. 1.08 mmol) of the compound from example 115, and the reaction mixture was stirred at 85° C. overnight. The mixture was concentrated, and the residue was stirred with dichloromethane and filtered. The solids were washed with dichloromethane and dried under high vacuum. 330 mg of the title compound were obtained (92% purity; 53% of theory).

Workup

  1. concentrationThe mixture was concentrated
  2. stirringthe residue was stirred with dichloromethane
  3. filtrationfiltered
  4. washThe solids were washed with dichloromethane
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-4312e30f779546ffa33023f7e7a9cea3
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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