1-Bromo-2-methylpropane → HCID 86731087, compound

HRID 1844419Notes

Reaction equation

HRID 1844419 reaction equation
[OH:1][C:2]1[C:3](=[O:17])[NH:4][C:5]2[C:10]([C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:25][CH:26]([CH3:28])[CH3:27]>CN(C=O)C>[CH2:25]([O:1][C:2]1[C:3](=[O:17])[N:4]([CH2:9][CH:10]([CH3:11])[CH3:5])[C:5]2[C:10]([C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:26]([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 10796Cesium carbonateHCID 300037ETHYL 3-HYDROXY-2-OXO-1,2-DIHYDROQUINOLINE-4-CARBOXYLATE

Product 1

HCID 86731087HCID 86731087, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 3-hydroxy-2-oxo-1,2-dihydroquinoline-4-carboxylate (250 mg, 1.07 mmol) in DMF (6 mL) was added cesium carbonate (908 mg, 2.79 mmol), 1-bromo-2-methylpropane (294 mg, 2.14 mmol). The reaction was heated at 50° C. for 16 h. The reaction mixture was allowed to cool to rt and washed with EtOAc. The organic phase was then washed with H2O and dried over Na2SO4 and concentrated in vacuo to give the crude product. Intermediate 28 was isolated via ISCO flash chromatography using a 40 g silica gel cartridge eluted with a 30-minute gradient from 0 to 100% EtOAc in hexane (350 mg, 1.01 mmol, 95% yield). LC-MS (ESI) m/z 346 (M+H), RT=2.30 min (Method B).

Workup

  1. temperatureto cool to rt
  2. washwashed with EtOAc
  3. washThe organic phase was then washed with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give the crude product

Sources & evidence

ORD record
ord-d02c5785b98046c0bed7d2519e003198
Source dataset
uspto-grants-2015_02
Patent number
US08946430B2

Reaction notes

Loading…