Methyl iodide → HCID 71547715, compound

HRID 570762Notes

Reaction equation

HRID 570762 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([Br:18])[C:3]=1[N:19]([CH3:39])[C:20]([C:22]1[C:23]([O:37][CH3:38])=[C:24]([NH:28][C:29]([C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[O:30])[CH:25]=[CH:26][CH:27]=1)=[O:21].[H-].[Na+].I[CH3:43]>CN(C)C=O.CO>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:9]([F:10])([F:11])[F:12])[C:13]([F:14])([F:15])[F:16])[CH:5]=[C:4]([Br:18])[C:3]=1[N:19]([CH3:39])[C:20]([C:22]1[C:23]([O:37][CH3:38])=[C:24]([N:28]([CH3:43])[C:29]([C:31]2[CH:32]=[CH:33][N:34]=[CH:35][CH:36]=2)=[O:30])[CH:25]=[CH:26][CH:27]=1)=[O:21]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 89488389HCID 89488389, compound

Product 1

HCID 71547715HCID 71547715, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6228DimethylformamideSolvent

Procedure

To the colorless solution of N-[3-[[2,6-dibromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-methyl-carbamoyl]-2-methoxy-phenyl]pyridine-4-carboxamide (example G-16 above) (0.120 g, 0.175 mmole) in N,N-dimethylformamide (5 ml), magnetically stirred under argon atmosphere was added sodium hydride (60% suspension in oil) (0.008 g, 0.192 mmole). After the gas evolution stopped, the resulting yellow solution was treated with iodomethane (0.012 ml, 0.027 g, 0.192 mmole). After 10 minutes, two drops of methanol was added and the reaction mixture was evaporated under reduced pressure. The residue was taken up in dichloromethane (5 ml) and water (10 ml). After phase separation, the aqueous solution was extracted twice with dichloromethane. The organic extracts were dried over sodium sulfate and evaporated. The residue was purified on a silica gel column using a gradient of ethyl acetate 20%-cyclohexane 80% to ethyl acetate 60%-cyclohexane 40%. The title product was a pale yellow oil showing, by LC-MS analysis (method 6 described hereunder) a retention time of 1.09 min and a M+H+ mass peak of 700.

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. customAfter phase separation
  3. extractionthe aqueous solution was extracted twice with dichloromethane
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. customevaporated
  6. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-d2f2ee90ab20489397058f144b71de64
Source dataset
uspto-grants-2015_05
Patent number
US09023873B2

Reaction notes

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