Boron trifluoride etherate → HCID 18784783, compound

HRID 1108524Notes

Reaction equation

HRID 1108524 reaction equation
O[CH:2]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]3=[O:24])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC.[Cl-].[NH4+]>ClCCl.C(OCC)C>[C:25]1([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([N:9]3[CH2:10][CH2:11][CH:12]([N:15]4[CH2:23][C:22]5[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=5)[C:16]4=[O:24])[CH2:13][CH2:14]3)=[CH:5][CH:4]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 25517Ammonium ChlorideHCID 18784785HCID 18784785, compound

Product 1

HCID 18784783HCID 18784783, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 278 compound (300 mg, 0.75 mmol) and triethylsilane (0.24 mL, 1.50 mmol) in dichloromethane (5 mL) at 0° C. was added dropwise a solution of boron trifluoride etherate (0.18 mL, 1.50 mmol). The reaction was stirred at RT overnight. Saturated ammonium chloride solution (2 mL) was added to quench the reaction. Ethyl ether (100 mL) was added and the organic layer was washed with water (2×30 mL), brine (2×30 mL) and dried over MgSO4. Purification was performed by flash chromatography on silica gel (50 g), loaded and eluted with 30% acetone in hexane. Pure fractions were combined and evaporated to give title compound (96 mg, 34%) as a white solid.

Workup

  1. customto quench
  2. customthe reaction
  3. washthe organic layer was washed with water (2×30 mL), brine (2×30 mL)
  4. dry with materialdried over MgSO4
  5. customPurification
  6. washeluted with 30% acetone in hexane
  7. customevaporated

Sources & evidence

ORD record
ord-2ff74207c9a040e696464ac484586d15
Source dataset
uspto-grants-2000_05
Patent number
US06066650

Reaction notes

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