HCID 86301015, compound → HCID 86301175, compound

HRID 1748383Notes

Reaction equation

HRID 1748383 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13](C(OCC)=O)[C:14]([CH3:18])=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C[Mg]Br>C1COCC1>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[C:13]([C:8]([OH:7])([CH3:17])[CH3:9])[C:14]([CH3:18])=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 86301015HCID 86301015, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 86301175HCID 86301175, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 7-((4-fluorobenzyl)oxy)-2-methylquinoline-3-carboxylate (Example 22, 65 mg, 0.19 mmol) in THF was added methyl magnesium bromide (3 M in Et2O, 0.5 mL, 1.5 mmol). The reaction was stirred for 30 minutes before being quenched with a sat. NH4Cl (aq.) solution. The aqueous layer was extracted with EtOAc. The organic layers were combined and concentrated onto silica. Purification (FCC, SiO2, 0-5%, MeOH/DCM) afforded the title compound as a yellow solid (28 mg, 45%). 1H NMR (400 MHz, CDCl3) δ 8.10 (s, 1H), 7.65 (d, J=8.6 Hz, 1H), 7.44 (dd, J=5.5, 8.2 Hz, 2H), 7.37 (d, J=2.0 Hz, 1H), 7.18 (dd, J=2.3, 9.0 Hz, 1H), 7.07 (t, J=8.6 Hz, 2H), 5.13 (s, 2H), 2.95 (s, 3H), 1.75 (s, 6H). [M+H]=326.3.

Workup

  1. custombefore being quenched with a sat. NH4Cl (aq.) solution
  2. extractionThe aqueous layer was extracted with EtOAc
  3. concentrationconcentrated onto silica
  4. customPurification (FCC, SiO2, 0-5%, MeOH/DCM)

Sources & evidence

ORD record
ord-0d74b68415d645e28d695068db5d3b56
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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