2-Aminopyridine → HCID 68443709, compound

HRID 332387Notes

Reaction equation

HRID 332387 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Cl[CH2:19][C:20]1[C:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:22][O:23][C:24]=1[CH3:25]>C1COCC1.C(OCC)(=O)C>[CH3:25][C:24]1[O:23][N:22]=[C:21]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]=1[CH2:19][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 104392-AminopyridineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 11052826Isoxazole, 4-(chloromethyl)-5-methyl-3-phenyl-

Product 1

HCID 68443709HCID 68443709, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-aminopyridine (109 mg, 1.2 mmol) in THF (2 mL) was added potassium bis(trimethylsilyl)amide (0.9 M in THF, 1.2 mL, 1.1 mmol) at 0° C. under argon. After 10 min, a solution of 4-chloromethyl-5-methyl-3-phenyl-isoxazole (200 mg, 1.0 mmol) in THF (1 mL) was added and the resulting mixture stirred at 0° C. for 1 h. The misture was then diluted with ethyl acetate (10 mL) and washed with water (10 mL) and brine (10 mL). The aqueous phase was extracted with ethyl acetate and the combined extracts dried over sodium sulfate, filtered and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=4:1: to 1:1) afforded the title compound (45 mg, 18%) as an off white solid. MS: m/e=266.2 [M+H]+.

Workup

  1. washwashed with water (10 mL) and brine (10 mL)
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined extracts dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate=4:1: to 1:1)

Sources & evidence

ORD record
ord-e6bf11f0a1d14320b2956e0185bee9cf
Source dataset
uspto-grants-2014_11
Patent number
US08877783B2

Reaction notes

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