Boron trifluoride etherate → HCID 69425076, compound

HRID 1351734Notes

Reaction equation

HRID 1351734 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:6]2[C:7]([CH2:15][CH2:16][O:17][Si](C(C)(C)C)(C)C)=[CH:8][NH:9][C:10]=2[C:11]([CH3:14])=[CH:12][CH:13]=1)=[O:4].[C:25]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])(=O)[CH2:26][CH2:27][CH3:28].B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:34]([O:33][C:31](=[O:32])[CH2:30][C:25]1([CH2:26][CH2:27][CH3:28])[C:8]2[NH:9][C:10]3[C:6]([C:7]=2[CH2:15][CH2:16][O:17]1)=[C:5]([C:3](=[O:4])[NH:2][CH3:1])[CH:13]=[CH:12][C:11]=3[CH3:14])[CH3:35]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 238498Ethyl 3-oxohexanoateHCID 69424164HCID 69424164, compound

Product 1

HCID 69425076HCID 69425076, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-methyl-1H-indole-4-carboxylic acid methylamide (100 mg, 0.289 mmol) and ethyl butyrylacetate (92 mL, 0.578 mmol) in CH2Cl2 (2 mL) was added BF3.OEt2 (0.11 mL, 0.867 mmol) dropwise at room temperature. After stirring overnight, the solution was diluted with CH2Cl2 (10 mL) and then washed with saturated aqueous NaHCO3 (10 mL) and brine (10 mL). The organic phase was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (silica, 50% EtOAc in hexanes) to give 88 mg (82%) of title compound as a yellow solid. 1H NMR (CDCl3): 300 MHz δ 9.54 (bs, 1H), 7.12 (d, J=7.38 Hz, 1H), 6.89 (d, J=7.38 Hz, 1H), 6.05 (d, J=4.71 Hz, 1H), 4.15 (m, 2H), 3.96 (m, 1H), 3.86 (m, 1H), 3.03–2.83 (m, 7H), 2.48 (s, 3H), 2.00 (m, 2H), 1.37 (m, 1H), 1.25 (t, J=6.84 Hz, 3H), 1.22 (m, 1H), 0.87 (t, J=7.17 Hz, 3H).

Workup

  1. washwashed with saturated aqueous NaHCO3 (10 mL) and brine (10 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (silica, 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4d8df123b5404747a68440d1c11bc736
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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