2-Methyltetrahydrofuran → HCID 131735049, compound

HRID 927199Notes

Reaction equation

HRID 927199 reaction equation
[H-].[Na+].[F:3][C:4]([F:19])([F:18])[C:5]1[CH:6]=[C:7]([NH:11][C:12]2[CH2:16][CH2:15][C:14](=[O:17])[CH:13]=2)[CH:8]=[CH:9][CH:10]=1.CC1CCCO1.[Br:26][C:27]1[CH:32]=[C:31]([C:33]#[N:34])[CH:30]=[CH:29][C:28]=1[N:35]([CH2:43]S(C1C=CC=CC=1)(=O)=O)[C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39]>O>[Br:26][C:27]1[CH:32]=[C:31]([C:33]#[N:34])[CH:30]=[CH:29][C:28]=1[N:35]([CH2:43][C:13]1[C:14](=[O:17])[CH2:15][CH2:16][C:12]=1[NH:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C:4]([F:18])([F:19])[F:3])[CH:6]=1)[C:36](=[O:42])[O:37][C:38]([CH3:39])([CH3:40])[CH3:41]

Participants

6

Reactant 4

HCID 73012-MethyltetrahydrofuranHCID 24758Sodium hydrideHCID 903110573-[3-(Trifluoromethyl)anilino]cyclopent-2-en-1-oneHCID 131735048Tert-butyl ((2-bromo-4-cyanophenyl)(phenylsulfonyl)methyl)carbamate

Product 1

HCID 131735049HCID 131735049, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% in mineral oil, 360 mg, 9.00 mmol) is added in portions to a mixture of 3-(3-(trifluoromethyl)phenylamino)cyclopent-2-enone (2.16 g, 8.96 mmol) and 2-methyltetrahydrofuran (30 mL). After 30 min tert-butyl (2-bromo-4-cyanophenyl)(phenyl-sulfonyl)methylcarbamate (Step 1, 3.35 g, 7.43 mmol) is added and the mixture is stirred at room temperature for 2 h. Water is added and the phases are separated. The aqueous phase is extracted twice with ethyl acetate, and the combined organic phases are washed with water, dried over MgSO4 and concentrated under reduced pressure. The residue is treated with tert-butyl methyl ether, and the mixture is stirred for 15 min. The precipitate is filtered, washed with tert-butyl methyl ether, and dried. Yield: 3.18 g. ESI mass spectrum: [(79Br)-M+H]+=550, [(81Br)-M+H]+=552; Retention time HPLC: 0.73 min (X012_S01).

Workup

  1. customthe phases are separated
  2. extractionThe aqueous phase is extracted twice with ethyl acetate
  3. washthe combined organic phases are washed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. additionThe residue is treated with tert-butyl methyl ether
  7. stirringthe mixture is stirred for 15 min
  8. filtrationThe precipitate is filtered
  9. washwashed with tert-butyl methyl ether
  10. customdried
  11. custom0.73 min (X012_S01)

Sources & evidence

ORD record
ord-5d00eab3aed94e938655f07e14c055c6
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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