HCID 85892012, compound → HCID 21099117, compound

HRID 1351742Notes

Reaction equation

HRID 1351742 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]=[O:14])=[CH:5][NH:6]2.[CH3:15][Mg+].[Br-]>C1COCC1>[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:14])[CH3:15])=[CH:5][NH:6]2

Participants

4

Reactant 2

HCID 85892012HCID 85892012, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 21099117HCID 21099117, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-bromo-7-fluoro-1H-indol-3-yl)-acetaldehyde (358 mg, 1.40 mmol) in THF (10 mL) was added a solution of MeMgBr (4.0 mL of 1.4 M in toluene-THF (75:25), 5.59 mmol) at room temperature. The mixture was stirred overnight at room temperature. The reaction mixture was quenched with H2O and extracted with EtOAc (3×20 mL). The combined organic phase was washed with brine (50 mL), dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (silica, 30% EtOAc in hexanes) to give 158 mg (42%) of the title compound as a white solid. 1H NMR (CDCl3): 300 MHz δ 8.97 (bs, 1H), 7.11 (dd, J=8.10, 4.20 Hz, 1H), 6.70 (dd, J=10.2, 8.10 Hz, 1H), 4.18 (m, 1H), 3.29(dd, J=14.5, 3.93 Hz, 1H), 2.87 (dd, J=14.5, 8.43 Hz, 1H), 2.16 (bs, 1H), 1.29 (d, J=6.18 Hz, 3H).

Workup

  1. customThe reaction mixture was quenched with H2O
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe combined organic phase was washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (silica, 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5cdc2d0a0d264a81b246e0c291397d5d
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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