Boron trifluoride etherate → HCID 69426395, compound

HRID 1351743Notes

Reaction equation

HRID 1351743 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[C:4]([CH2:12][CH:13]([OH:15])[CH3:14])=[CH:5][NH:6]2.[C:16]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])(=O)[CH2:17][CH2:18][CH3:19].B(F)(F)F.CCOCC>C(Cl)Cl>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][C:16]1([CH2:17][CH2:18][CH3:19])[C:5]2[NH:6][C:7]3[C:3]([C:4]=2[CH2:12][CH:13]([CH3:14])[O:15]1)=[C:2]([Br:1])[CH:10]=[CH:9][C:8]=3[F:11])[CH3:26]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 238498Ethyl 3-oxohexanoateHCID 21099117HCID 21099117, compound

Product 1

HCID 69426395HCID 69426395, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(4-bromo-7-fluoro-1H-indol-3-yl)-propan-2-ol (155 mg, 0.570 mmol) and ethyl butyrylacetate (0.137 mL, 0.854 mmol) in CH2Cl2 (3 mL) was added BF3.OEt2 (0.11 mL, 0.854 mmol) dropwise at room temperature. After stirring for 3 hours, the mixture was diluted with CH2Cl2 (15 mL) and then washed with saturated aqueous NaHCO3 (15 mL) and brine (15 mL). The organic phase was dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (silica, 10% EtOAc in hexanes) to give (5-bromo-8-fluoro-3-methyl-1-propyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid ethyl ester as a pale yellow solid (this sample contains ethyl butyrylacetate).

Workup

  1. washwashed with saturated aqueous NaHCO3 (15 mL) and brine (15 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (silica, 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-431ad2fac89d4169b1a931647a863d5a
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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