Hexane → HCID 23144622, compound

HRID 1361812Notes

Reaction equation

HRID 1361812 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1.C([Li])CCC.CCCCCC.[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26]1[N:27]=[C:28]([NH:37][C:38]([C:40]2[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=2)=[O:39])[S:29][C:30]=1[C:31](=[O:36])N(OC)C.[Cl-].[NH4+]>C1COCC1>[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26]1[N:27]=[C:28]([NH:37][C:38]([C:40]2[CH:41]=[CH:42][N:43]=[CH:44][CH:45]=2)=[O:39])[S:29][C:30]=1[C:31]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1)=[O:36]

Participants

7

Reactant 5

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 2568102-Bromo-6-methoxypyridineHCID 23144082HCID 23144082, compoundHCID 178418339Butyllithium

Product 1

HCID 23144622HCID 23144622, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

2-Bromo-6-methoxypyridine (0.274 mL, 2.23 mmol) was dissolved in THF (1 mL), and a 1.58 mol/L solution of n-butyllithium in n-hexane (1.42 mL, 2.23 mmol) was added thereto in a stream of argon at −78° C., followed by stirring for 15 minutes at −78° C. A solution of Compound 98 (200 mg, 0.558 mmol) in THF (2 mL) was added dropwise to the reaction mixture, followed by stirring at room temperature for 1.5 hours. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:9) to afford the entitled Compound 283 (77.0 mg, 34%).

Workup

  1. customat −78° C.
  2. stirringby stirring at room temperature for 1.5 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away under reduced pressure
  7. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:9)

Sources & evidence

ORD record
ord-2b389c45e8f24384b1984b8bbe556077
Source dataset
uspto-grants-2011_02
Patent number
US07880013B2

Reaction notes

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