Dimethyl Sulfide → HCID 89964578, compound

HRID 1846229Notes

Reaction equation

HRID 1846229 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)N(C(OC(C)(C)C)=O)[CH2:4][CH2:3]1.[CH2:19]=[C:20]1[C:26]2=NC=CC=C2OCC[CH2:21]1.[C:31]([O-])(O)=[O:32].[Na+].CSC>CCOC(C)=O.O.C(Cl)(Cl)Cl.CO>[C:20]([C:9]1[N:10]=[C:11]2[C:2](=[O:1])[CH2:3][CH2:4][CH2:31][O:32][C:6]2=[CH:7][CH:8]=1)([CH3:26])([CH3:21])[CH3:19]

Participants

9

Reactant 4

HCID 1068Dimethyl SulfideHCID 516892Sodium BicarbonateHCID 89964241HCID 89964241, compoundHCID 89964768HCID 89964768, compound

Product 1

HCID 89964578HCID 89964578, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

tert-butyl 4-oxo-3,4-dihydro-1,5-naphthyridine-1(2H)-carboxylate. To a solution of 9-methylene-6,7,8,9-tetrahydrooxepino[3,2-b]pyridine (1 eq.) in a mixture of solvents (MeOH:CHCl3) is added a catalytic amount of NaHCO3. The reaction mixture is cooled to −78° C. and purged with O3. Reaction progress is monitored by TLC. After the reaction is judged complete, the reaction mixture is quenched with dimethyl sulfide (5 eq.) at −78° C. The resulting mixture is stirred for 12 h at ambient temperature. The reaction mixture is diluted with EtOAc and water. The organic layer is washed with water, dried over Na2SO4, and concentrated in vacuo. The compound that may be thus obtained is purified by column chromatography to give the title compound.

Workup

  1. custompurged with O3
  2. customReaction progress
  3. washThe organic layer is washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe compound that may be thus obtained
  7. customis purified by column chromatography

Sources & evidence

ORD record
ord-73ae112563af42bf9a1cfb4e00886e66
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

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