Tetrabutylammonium Fluoride → HCID 69015560, compound

HRID 1436489Notes

Reaction equation

HRID 1436489 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH2:4][C@H:5]([CH:21]=[O:22])[N:6]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:7]2.[F:23][C:24]1[CH:25]=[C:26]([CH2:31][CH2:32][N+:33]([O-:35])=[O:34])[CH:27]=[C:28]([F:30])[CH:29]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C.O.[Cl-].[Na+]>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH2:4][C@H:5]([C@@H:21]([OH:22])[C@@H:32]([N+:33]([O-:35])=[O:34])[CH2:31][C:26]1[CH:25]=[C:24]([F:23])[CH:29]=[C:28]([F:30])[CH:27]=1)[N:6]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH2:7]2

Participants

8

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 552507531,3-Difluoro-5-(2-nitroethyl)benzeneHCID 86615373HCID 86615373, compound

Product 1

HCID 69015560HCID 69015560, compoundYield 38.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve tert-butyl 5-bromo-3(R)-formyl-8-methoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate (400.0 mg, 0.001080 mol) and 1-(3,5-difluorophenyl)-2-nitroethane (305 mg, 0.00162) in tetrahydrofuran (3.00 mL) and cool to 0° C. celsius. Add 1.00 M tetra-n-butylammonium fluoride in tetrahydrofuran (1.48 mL) and stir at 0° C. for 40 minutes. Dilute the reaction mixture with ethyl acetate (75 mL), water (20 mL) and saturated aqueous sodium chloride (5 mL). Shake well and separate the layers. Wash the organic layer with water (2×25 mL), saturated aqueous sodium chloride (1×25 mL) and dry over magnesium sulfate. Purify (Biotage medium pressure chromatography eluting with 10% ethyl acetate:hexanes) to give the desired product (234 mg, 37%) as a white solid.

Workup

  1. customShake well and separate the layers
  2. washWash the organic layer with water (2×25 mL), saturated aqueous sodium chloride (1×25 mL)
  3. dry with materialdry over magnesium sulfate
  4. customPurify
  5. wash(Biotage medium pressure chromatography eluting with 10% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-91f0713fbbae4019a12021335be81bd8
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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