3-Pentanamine → HCID 178446212, compound

HRID 2262680Notes

Reaction equation

HRID 2262680 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](F)[C:5]([N+:8]([O-])=O)=[N:6][CH:7]=1.[NH2:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15].O.O.[Sn](Cl)Cl.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[N:12]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[C:23]([OH:24])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 120193-PentanamineHCID 61436Stannous chloride dihydrateHCID 682631,1'-CarbonyldiimidazoleHCID 534389645-Chloro-3-fluoro-2-nitropyridine

Product 1

HCID 178446212HCID 178446212, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 30 mL scintillation vial equipped with a stir bar was added ethyl acetate (10 mL), 5-chloro-3-fluoro-2-nitropyridine (101 mg, 0.56 mmol), and 3-aminopentane (74 mL, 0.63 mmol). The reaction was stirred at room temperature until starting material was consumed (TLC 25% ethyl acetate in hexanes). To this solution was added tin(II) chloride dihydrate (560 mg, 2.5 mmol), and the mixture was stirred until the aryl nitro was completely reduced (4 h to overnight). The solution was transferred from the scintillation vial to a 5 mL microwave tube, followed by the addition of carbonyldiimidazole (>10 equiv). The reaction was heated in a microwave reactor at 150° C. for 20 min. After cooling, water was added, and the organic layer was separated, concentrated, and purified by flash chromatography over silica gel (30-40% ethyl acetate in hexanes) to give 6-chloro-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyridin-2-ol (93 mg, 0.390 mmol, 68% yield).

Workup

  1. customIn a 30 mL scintillation vial equipped with a stir bar
  2. customwas consumed (TLC 25% ethyl acetate in hexanes)
  3. custom(4 h to overnight)
  4. customThe solution was transferred from the scintillation vial to a 5 mL microwave tube
  5. temperatureThe reaction was heated in a microwave reactor at 150° C. for 20 min
  6. temperatureAfter cooling
  7. customthe organic layer was separated
  8. concentrationconcentrated
  9. custompurified by flash chromatography over silica gel (30-40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3ab4a6b0bdbe41a38ccb8d603524ec01
Source dataset
uspto-grants-2010_12
Patent number
US07851484B2

Reaction notes

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