HCID 12191680, compound → HCID 68182246, compound

HRID 1620276Notes

Reaction equation

HRID 1620276 reaction equation
Cl[C:2]1[C:11]([CH:12]2[O:16][CH2:15][CH2:14][O:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:17][CH3:18])[CH:8]=2)[N:3]=1.[CH2:19]([Mg]Cl)[CH2:20][CH2:21][CH3:22]>C1COCC1>[CH2:19]([C:2]1[C:11]([CH:12]2[O:16][CH2:15][CH2:14][O:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:17][CH3:18])[CH:8]=2)[N:3]=1)[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 12191680HCID 12191680, compound2×HCID 178418265HCID 178418265, compound

Product 1

HCID 68182246HCID 68182246, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-chloro-3-(1,3-dioxolan-2-yl)-6-methoxyquinoline SMA 44002 (1.41 g, 5.31 mmol) in dry THF (27 mL) at 0° C. under N2 in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added Fe(acac)3 (197 mg, 0.547 mmol) followed by dropwise addition of n-butylmagnesium chloride (2.0 M in THF, 12.4 mL, 24.8 mmol). After complete addition, the mixture was stirred for 5 h at 70° C. then cooled to RT and quenched with water (10 mL). THF was then removed at 40° C. under vacuum and the resulting mixture was extracted with CH2Cl2 (50 mL). The organic phase was isolated, washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent CH2Cl2:EtOAc=100:0 to 95:5) gave 2-butyl-3-(1,3-dioxolan-2-yl)-6-methoxyquinoline SMA 44042 as an orange oil (867 mg, 57% yield).

Workup

  1. additionAfter complete addition
  2. temperaturethen cooled to RT
  3. customquenched with water (10 mL)
  4. customTHF was then removed at 40° C. under vacuum
  5. extractionthe resulting mixture was extracted with CH2Cl2 (50 mL)
  6. customThe organic phase was isolated
  7. washwashed with brine (10 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated at 40° C. under vacuum
  11. customPurification by column chromatography (SiO2, eluent CH2Cl2:EtOAc=100:0 to 95:5)

Sources & evidence

ORD record
ord-c9436491b4ee4689b9ab9cb046f82eb9
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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