Boron trifluoride etherate → HCID 18784783, compound

HRID 1418725Notes

Reaction equation

HRID 1418725 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-c1acafb1f371424bbfe6fba4e103ada4
Source dataset
uspto-grants-1999_03
Patent number
US05883099

Reaction notes

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