Lithium Chloride → HCID 178516563, compound

HRID 575808Notes

Reaction equation

HRID 575808 reaction equation
[Br:1][C:2]1[C:3]([O:10][CH2:11][CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:5]([O:8]C)=[N:6][CH:7]=1.[Li+].[Cl-].S(O)(C1C=CC(C)=CC=1)(=O)=O.O>CN(C=O)C.O>[Br:1][C:2]1[C:3]([O:10][CH2:11][CH:12]2[CH2:13][CH2:14]2)=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 1180238475-Bromo-4-(cyclopropylmethoxy)-2-methoxypyridine

Product 1

HCID 178516563HCID 178516563, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of the title compound from step 1 (450 mg, 1.74 mmol) in DMF (5 mL) was added LiCl (370 mg, 8.72 mmol) and TsOH H2O (1.52 g, 8.72 mmol) at room temperature. The mixture was heated to 120° C. and stirred for 1 hour. The mixture was diluted with water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic phase was washed with saturated brine (2×200 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the title compound (380 mg, yield: 88.9%) as yellow solid which used directly for the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 7.49 (s, 1H), 5.91 (s, 1H), 3.87 (d, J=6.8 Hz, 2H), 1.36-1.22 (m, 1H), 0.71-0.67 (m, 2H), 0.46-0.42 (m, 2H). LCMS: 244.0 (M+1)+; 246.0

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. washThe combined organic phase was washed with saturated brine (2×200 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c576aeeacc0549368c7964ee9c5168a2
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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