HCID 66699272, compound → HCID 24830535, compound

HRID 2092135Notes

Reaction equation

HRID 2092135 reaction equation
C[Mg]Br.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([C:23]3[N:28]=[CH:27][C:26]([C:29]4[O:33][N:32]=[C:31](C(OCC)=O)[CH:30]=4)=[CH:25][CH:24]=3)([CH3:22])[CH:19]([CH3:21])[CH3:20])=[CH:14][CH:13]=2)[CH:9]=[N:10][CH:11]=1>C1(C)C=CC=CC=1.C1COCC1.C1COCC1>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([C:23]3[N:28]=[CH:27][C:26]([C:29]4[O:33][N:32]=[C:31]([C:6]([OH:5])([CH3:7])[CH3:11])[CH:30]=4)=[CH:25][CH:24]=3)([CH3:22])[CH:19]([CH3:20])[CH3:21])=[CH:14][CH:13]=2)[CH:9]=[N:10][CH:11]=1

Participants

5

Reactant 2

HCID 66699272HCID 66699272, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 24830535HCID 24830535, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

Methyl magnesium bromide (300 μL of a 1.4M solution in toluene:THF (75:25), 0.420 mmol) was added to a stirred solution of 3b (40.0 mg, 0.0850 mmol) in THF (2.00 mL) at 0° C. After approximately 3 h, the reaction was quenched with saturated aqueous ammonium chloride and extracted three times with EtOAc. The combined organic extracts were washed with water and brine, dried (magnesium sulfate) and concentrated in vacuo. The crude residue was purified by preparative thin-layer chromatography on silica gel (60% EtOAc/hexanes as eluent) to afford the title compound 3c. m/z (ES) 458 (MH)+. 1HNMR (500 MHz, CDCl3): δ 9.02 (m, 1H), 8.46 (m, 1H), 8.29 (m, 1H), 7.96 (m, 1H), 7.51 (m, 4H), 7.38 (m, 2H), 6.62 (s, 1H), 3.92 (s, 3H), 3.18 (m, 1H), 1.78 (s, 3H), 1.69 (s, 6H), 0.91 (d, 3H, J=6.6 Hz), 0.88 (d, 3H, J=6.9 Hz).

Workup

  1. customthe reaction was quenched with saturated aqueous ammonium chloride
  2. extractionextracted three times with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by preparative thin-layer chromatography on silica gel (60% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-2f4ca8b2fcf648cb8489fba0d972eec8
Source dataset
uspto-grants-2013_05
Patent number
US08440672B2

Reaction notes

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