p-Toluenesulfonic acid → HCID 18771920, compound

HRID 460224Notes

Reaction equation

HRID 460224 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:4][CH:3]=1.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[Br:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH2:11][O:12][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][O:13]2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 18771745HCID 18771745, compound

Product 1

HCID 18771920HCID 18771920, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(6-bromo-pyridin-2-ylamino)-propan-1-ol (4.2 g, 18 mmol), 3,4-dihydro-2H-pyran (1.6 mL, 18 mmol), TsOH (0.34 g, 1.8 mmol) and CH2Cl2 (100 mL) were stirred at RT. After 15 h, the reaction was quenched with saturated NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to give the desired compound as a pale-yellow oil. MS m/z: 316.0 (M+H). Calc'd for C13H19BrN2O2 315.21.

Workup

  1. customthe reaction was quenched with saturated NaHCO3
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad096a5bdd77466c9cbbf2ef9b6534d7
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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