Boron trifluoride → HCID 57438344, compound

HRID 1818506Notes

Reaction equation

HRID 1818506 reaction equation
[OH:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19](O)[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]4[N:27]=[N:28][NH:29][N:30]=4)[CH:21]=3)=[CH:15][CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:32](=[O:34])[CH3:33].[SiH](CC)(CC)CC.B(F)(F)F>C(Cl)Cl>[OH:1][C:2]1[C:7]([CH:8]([CH3:9])[CH3:10])=[C:6]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]4[N:27]=[N:28][NH:29][N:30]=4)[CH:21]=3)=[CH:17][CH:18]=2)[CH:5]=[CH:4][C:3]=1[C:32](=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 12052TriethylsilaneHCID 11676931HCID 11676931, compound

Product 1

HCID 57438344HCID 57438344, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-[2-Hydroxy-4-(4-{hydroxy-[3-(2H-tetrazol-5-yl)-phenyl]-methyl}-benzyloxy)-3-isopropyl-phenyl]-ethanone (100 mg, 0.22 mmol) in anhydrous CH2Cl2 (5.4 mL) is added Et3SiH (281 μL, 1.76 mmol) and BF3.ether complex (56 μL, 0.44 mmol). The reaction mixture is stirred for 1.5 h. The reaction mixture is quenched into saturated aqueous NH4Cl (10 mL) and extracted with a 50% tetrahydrofuran/ethyl acetate solution (3×30 mL). The organic layers are combined, washed with brine, dried over sodium sulfatesodium sulfate, and concentrated to an oil. The residue is purified by reverse phase HPLC using a gradient of 90:10 to 20:80 (H2O/0.1% TFA):CH3CN as eluent to give the title compound (29 mg, 30%). LC-MS (m/e): 441 (M−1); 1H NMR (DMSO-d6) δ 13.1 (1H, s), 7.82-8.00 (2H, m), 7.78 (1H, d), 7.30-7.55 (6H, m), 6.72 (1H, d), 5.22 (2H, s), 4.08 (2H, s), 3.57 (1H, m), 2.57 (3H, s), 1.26 (3H, s), 1.23 (3H, s).

Workup

  1. customThe reaction mixture is quenched into saturated aqueous NH4Cl (10 mL)
  2. extractionextracted with a 50% tetrahydrofuran/ethyl acetate solution (3×30 mL)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfatesodium sulfate
  5. concentrationconcentrated to an oil
  6. customThe residue is purified by reverse phase HPLC

Sources & evidence

ORD record
ord-27eea310079645e8b76609b9e9d8dfd7
Source dataset
uspto-grants-2009_10
Patent number
US07598423B2

Reaction notes

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