3-Bromo-1-methyl-1,2-dihydroquinolin-2-one → HCID 131735819, compound

HRID 2205671Notes

Reaction equation

HRID 2205671 reaction equation
Br[C:2]1[C:3](=[O:13])[N:4]([CH3:12])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:14]([O:18][C:19](=[O:28])[NH:20][CH2:21][C:22](N(OC)C)=[O:23])([CH3:17])([CH3:16])[CH3:15].C([Mg]Cl)(C)C>C1COCC1.ClCCl>[C:14]([O:18][C:19](=[O:28])[NH:20][CH2:21][C:22]([C:2]1[C:3](=[O:13])[N:4]([CH3:12])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:23])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 3

HCID 2683153-Bromo-1-methyl-1,2-dihydroquinolin-2-oneHCID 4428209tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamateHCID 178418918HCID 178418918, compound

Product 1

HCID 131735819HCID 131735819, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 0.3 M solution of 3-bromo-1-methylquinolin-2(1 H)-one (1 equiv; prepared as described in Tetrahedron, 64 (26), 6030-6037; 2008) and tert-butyl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate (1.2 eq) in dry THF, isopropylmagnesium chloride (3 eq) was added dropwise at room temperature. The mixture was stirred for 30 min at room temperature, diluted with dichloromethane, washed with sat. aq. NH4Cl dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, Pethroleum ether/EtOAc, from 7% to 60% EtOAc). The pooled fractions were concentraded under vacuum to the title compound. MS (ES) C17H20N2O4 requires: 316.35, found: 317. 1H-NMR (400 MHz, DMSO-d6) δ: 8.53 (1 H, s), 7.99 (1 H, d, J=7.2 Hz), 7.78 (1 H, t, J=6.8 Hz), 7.61 (1 H, d, J=8.4 Hz), 7.35 (1 H, t, J=7.2 Hz), 6.97 (1 H, bt, J=5.6 Hz), 4.45 (1 H, d, J=5.6 Hz), 3.70 (3 H, s), 1.39 (9 H, s).

Workup

  1. washwashed with sat. aq. NH4Cl
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (SiO2, Pethroleum ether/EtOAc, from 7% to 60% EtOAc)

Sources & evidence

ORD record
ord-9acd58db10164f208a3877e76c4f4152
Source dataset
uspto-grants-2016_06
Patent number
US09371295B2

Reaction notes

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