Iodine → HCID 87085197, compound

HRID 510068Notes

Reaction equation

HRID 510068 reaction equation
N[C:2]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:8]=[C:7]2[C:3]=1[N:4]([CH:29]1[CH2:32][N:31]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:30]1)[C:5](=[O:28])[NH:6]2.[I-:40].[Cs+].II.N(OCCC(C)C)=O>COCCOC.[Cu]I>[F:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][N:13]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:19]2[C:11]([C:9]2[N:8]=[C:7]3[C:3]([N:4]([CH:29]4[CH2:32][N:31]([C:33]([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34])[CH2:30]4)[C:5](=[O:28])[NH:6]3)=[C:2]([I:40])[N:10]=2)=[N:12]1

Participants

7

Reactant 4

HCID 807IodineHCID 8053Isoamyl NitriteHCID 24601Cesium iodideHCID 66635319HCID 66635319, compound

Product 1

HCID 87085197HCID 87085197, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
60 °C

Procedure

1.788 g (3.364 mmol) of the compound from example 96A were initially charged in 20 ml of 1,2-dimethoxyethane and then admixed at RT with 873 mg (3.364 mmol) of cesium iodide, 426 mg (1.682 mmol) of iodine and 192 mg (1.009 mmol) of copper(I) iodide. After addition of 2.961 ml of isopentyl nitrite, the mixture was heated to 60° C. overnight. After cooling, a precipitate was filtered off and washed with ethyl acetate. Subsequently, water was added to the precipitate, the mixture was stirred and then the precipitate was again filtered off with suction and washed with a little water and acetonitrile. 0.373 g (17% of theory) of the title compound were obtained after drying under high vacuum.

Workup

  1. temperatureAfter cooling
  2. filtrationa precipitate was filtered off
  3. washwashed with ethyl acetate
  4. additionSubsequently, water was added to the precipitate
  5. filtrationthe precipitate was again filtered off with suction
  6. washwashed with a little water and acetonitrile

Sources & evidence

ORD record
ord-af1f6daa80af4ec28158534b29871953
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

Loading…