Ethyl Bromide → HCID 56962757, compound

HRID 2038407Notes

Reaction equation

HRID 2038407 reaction equation
[C:1]1([C:7]([N:9]2[CH2:13][CH2:12][C@H:11]([NH:14][CH:15]3[CH2:18][N:17]([C:19]([C:21]4[CH:26]=[CH:25][C:24]([C:27]5[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=5)=[CH:23][CH:22]=4)=[O:20])[CH2:16]3)[CH2:10]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:39](Br)[CH3:40]>CN(C=O)C.CCOC(C)=O.O>[CH2:39]([N:14]([CH:15]1[CH2:16][N:17]([C:19]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=3)=[CH:23][CH:22]=2)=[O:20])[CH2:18]1)[C@H:11]1[CH2:12][CH2:13][N:9]([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:8])[CH2:10]1)[CH3:40]

Participants

7

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 67288595HCID 67288595, compound

Product 1

HCID 56962757HCID 56962757, compoundYield 17.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Compound 16 (50 mg, 0.101 mmol) in dry DMF (1 mL) was added NaH (6 mg, 0.152 mmol) and the resulting mixture was stirred at room temperature for 20 min. EtBr (0.012 mL, 0.12 mmol) was added and the reaction mixture was heated to 130° C. overnight. The resultant mixture was diluted with EtOAc and water. The organic layer was washed with water and aq. NaHCO3, dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification of the residue by flash column chromatography (silica gel, 5% MeOH/EtOAc+0.5 TEA %) gave compound 53 (9 mg). MS m/z (M+H+) 522.0.

Workup

  1. temperaturethe reaction mixture was heated to 130° C. overnight
  2. washThe organic layer was washed with water and aq. NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by flash column chromatography (silica gel, 5% MeOH/EtOAc+0.5 TEA %)

Sources & evidence

ORD record
ord-1610a4b1454d4db2bb000d96db544a22
Source dataset
uspto-grants-2013_11
Patent number
US08575363B2

Reaction notes

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