Triethyl phosphite → HCID 117728170, compound

HRID 1772682Notes

Reaction equation

HRID 1772682 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[P:18]([O:25]CC)([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]>>[CH2:20]([O:19][P:18]([CH2:2][C:3]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)([O:22][CH2:23][CH3:24])=[O:25])[CH3:21]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 117727907HCID 117727907, compound

Product 1

HCID 117728170HCID 117728170, compound

Conditions

Temperature
100 °C

Procedure

Ethyl 2-(bromomethyl)quinoline-4-carboxylate (1.0 g, 3.4 mmol, as prepared above) was treated with triethyl phosphite (11.3 g, 68.0 mmol) and the resultant slurry was heated to 100° C. overnight. The reaction was concentrated under reduced pressure, diluted with DCM (50 mL), washed with sodium bicarbonate, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (0:100-1:1 EtOAc/heptane) to afford compound 45a. Mass spectrum (LCMS, ESI pos.) Calcd. For C17H22NO5P: 352.1 (M+H). found 352.2.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additiondiluted with DCM (50 mL)
  3. washwashed with sodium bicarbonate
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel (0:100-1:1 EtOAc/heptane)

Sources & evidence

ORD record
ord-de14144fc4814aa598d7a72ac020e001
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

Loading…