2-Aminopyridine → HCID 70818472, compound

HRID 591024Notes

Reaction equation

HRID 591024 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:14]=1)=O.BrCC(C1C2OCCCC=2C=CC=1)=O.[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1>C(O)C>[O:13]1[C:8]2[CH:7]=[CH:6][C:5]([C:3]3[N:29]=[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]4[CH:2]=3)=[CH:14][C:9]=2[CH2:10][CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 104392-AminopyridineHCID 9992510HCID 9992510, compoundHCID 86717836HCID 86717836, compound

Product 1

HCID 70818472HCID 70818472, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of the 80/20 mixture of 2-bromo-1-(3,4-dihydro-2H-1-benzopyran-6-yl)ethan-1-one (19a) and 2-bromo-1-(3,4-dihydro-2H-1-benzopyran-8-yl)ethan-1-one (450 mg, 1.76 mmol) and 2-aminopyridine (166 mg, 1.76 mmol) in ethanol (10 mL) was heated at 60° C. overnight. The mixture was concentrated in vacuo. A 1M solution of sodium hydroxide (10 mL) and ethyl acetate (10 mL) were added. The aqueous layer was extracted with ethyl acetate (10 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 40/60) to provide the desired imidazo-pyridine (19b) (228 mg, 0.91 mmol, 64%) as a beige solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionA 1M solution of sodium hydroxide (10 mL) and ethyl acetate (10 mL) were added
  3. extractionThe aqueous layer was extracted with ethyl acetate (10 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 40/60)

Sources & evidence

ORD record
ord-22b2d2aa1fc5486fa09c1eccb1044ad3
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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