Triethyl phosphite → Ethyl 2-[(diethoxyphosphinyl)methyl]-5-quinolinecarboxylate

HRID 718691Notes

Reaction equation

HRID 718691 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]=1.[P:18]([O:25]CC)([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]>>[CH2:16]([O:15][C:13]([C:9]1[C:10]2[CH:11]=[CH:12][C:3]([CH2:2][P:18]([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])=[O:25])=[N:4][C:5]=2[CH:6]=[CH:7][CH:8]=1)=[O:14])[CH3:17]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 117728675Ethyl 2-(bromomethyl)quinoline-5-carboxylate

Product 1

HCID 117732530Ethyl 2-[(diethoxyphosphinyl)methyl]-5-quinolinecarboxylate

Conditions

Temperature
110 °C

Procedure

Compound 73c (240 mg, 0.816 mmol) was treated with triethyl phosphite (2.12 mL, 12.2 mmol) and the resultant slurry was heated to 110° C. for 4 h. The reaction was concentrated in vacuo, diluted with DCM (50 mL), washed with sodium bicarbonate, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by preparative TLC (10% MeOH/DCM) to afford compound 73d as an oil. Mass spectrum (LCMS, ESI pos.) Calcd. For C17H22NO5P: 352.1 (M+H). found 352.2.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with DCM (50 mL)
  3. washwashed with sodium bicarbonate
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative TLC (10% MeOH/DCM)

Sources & evidence

ORD record
ord-55dee56b1b694cb89f0c7142b52e9847
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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