2-Bromopyridine → HCID 131732405, compound

HRID 1841838Notes

Reaction equation

HRID 1841838 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Mg]Cl)(C)C.[C:13]([C@:16]1([CH2:44][OH:45])[O:22][C@@:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([CH:30]=[O:31])=[CH:26][CH:25]=2)([OH:21])[C@:19]([C:33](=[O:35])[CH3:34])([OH:32])[C@@:18]([C:37](=[O:39])[CH3:38])([OH:36])[C@@:17]1([C:41](=[O:43])[CH3:42])[OH:40])(=[O:15])[CH3:14].[NH4+].[Cl-]>C1COCC1>[C:13]([C@:16]1([CH2:44][OH:45])[O:22][C@@:20]([O:23][C:24]2[CH:25]=[CH:26][C:27]([CH:30]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=3)[OH:31])=[CH:28][CH:29]=2)([OH:21])[C@:19]([C:33](=[O:35])[CH3:34])([OH:32])[C@@:18]([C:37](=[O:39])[CH3:38])([OH:36])[C@@:17]1([C:41](=[O:43])[CH3:42])[OH:40])(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 79732-BromopyridineHCID 25517Ammonium ChlorideHCID 131732406HCID 131732406, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 131732405HCID 131732405, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Bromopyridine (726 mg, 440 μl, 4.6 mmol) is dissolved in 5 ml of THF at ambient temperature. Isopropylmagnesium chloride (2.3 ml, 4.6 mmol, 2M in THF) is added dropwise under argon and the mixture is left stirring for 2 hours. This solution is added to a solution of tetraacetyl-(p-formylphenoxy)-β-galactose (2.07 g, 4.6 mmol) in 3 ml of THF at ambient temperature. The mixture is left stirring for 18 h and then a saturated NH4Cl solution is slowly added. The resulting aqueous solution is extracted with ethyl acetate. The organic phase is dried over Na2SO4 and evaporated under vacuum. The crude reaction product is purified by chromatography on silica gel (ether/pentane 2/1 pure ether). A yellow solid is then obtained (600 mg, yield 25%).

Workup

  1. waitthe mixture is left
  2. waitThe mixture is left
  3. stirringstirring for 18 h
  4. extractionThe resulting aqueous solution is extracted with ethyl acetate
  5. dry with materialThe organic phase is dried over Na2SO4
  6. customevaporated under vacuum
  7. customThe crude reaction product
  8. customis purified by chromatography on silica gel (ether/pentane 2/1 pure ether)
  9. customA yellow solid is then obtained (600 mg, yield 25%)

Sources & evidence

ORD record
ord-7c21f2a8f03947a080178f64194575d1
Source dataset
uspto-grants-2015_02
Patent number
US08945514B2

Reaction notes

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