1,3,5-Trifluorobenzene → HCID 178464146, compound

HRID 1170439Notes

Reaction equation

HRID 1170439 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[CH:3]=1.C([N-]C(C)C)(C)C.[Li+].[CH2:18]([N:20]([CH2:42][CH3:43])[C@H:21]1[CH2:24][C@H:23]([CH2:25][N:26]2[C:34]3[C:29](=[C:30]([C:36]([F:39])([F:38])[F:37])[CH:31]=[C:32]([I:35])[CH:33]=3)[C:28](=[O:40])[C:27]2=[O:41])[CH2:22]1)[CH3:19].C(=O)(O)[O-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[C:28]1([OH:40])[C:29]2[C:34](=[CH:33][C:32]([I:35])=[CH:31][C:30]=2[C:36]([F:38])([F:39])[F:37])[N:26]([CH2:25][C@H:23]2[CH2:22][C@H:21]([N:20]([CH2:18][CH3:19])[CH2:42][CH3:43])[CH2:24]2)[C:27]1=[O:41]

Participants

6

Reactant 4

HCID 97451,3,5-TrifluorobenzeneHCID 516892Sodium BicarbonateHCID 2724682Lithium diisopropylamideHCID 178464130HCID 178464130, compound

Product 1

HCID 178464146HCID 178464146, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,3,5-trifluorobenzene (318 mg, 2.41 mmol) in tetrahydrofuran (6.0 mL) was cooled to 78° C. under nitrogen, and thereto was added dropwise 2N lithium diisopropylamide (1.53 mL, 3.06 mmol), and the mixture was stirred for 30 minutes, Then, thereto was added dropwise a solution of the compound of Example 1-1 (650 mg, 1.34 mmol) in tetrahydrofuran (16 mL), and the mixture was stirred at −78° C. for 3 hours. To the reaction solution was added saturated aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate, dried over magnesium sulfate and filtered. The filtrate was evaporated and purified by silica gel column chromatography (hexane/ethyl acetate/ammonia water=50/1/0.25 to 30/1/0.16 to 20/1/0.1) to give the titled compound (223 mg, 27%).

Workup

  1. stirringthe mixture was stirred at −78° C. for 3 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. custompurified by silica gel column chromatography (hexane/ethyl acetate/ammonia water=50/1/0.25 to 30/1/0.16 to 20/1/0.1)

Sources & evidence

ORD record
ord-06835bc7a0934ab083bc7caceb71ca91
Source dataset
uspto-grants-2010_11
Patent number
US07825155B2

Reaction notes

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