2-Aminopyridine → HCID 21071444, compound

HRID 1666901Notes

Reaction equation

HRID 1666901 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Br[C:9]1[CH:10]=[C:11]([CH:15]2[O:19][CH2:18][CH2:17][O:16]2)[CH:12]=[CH:13][CH:14]=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>CCOCC.C1(C)C=CC=CC=1>[O:16]1[CH2:17][CH2:18][O:19][CH:15]1[C:11]1[CH:10]=[C:9]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 104392-AminopyridineHCID 873062-(3-Bromophenyl)-1,3-dioxolaneHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 21071444HCID 21071444, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

Combine 2-aminopyridine (8.25 g, 95 mmol), 2-(3-bromo-phenyl)-[1,3]dioxolane (13.8 mL, 90 mmol), sodium t-butoxide (12.2 g, 126 mmol), BINAP (210 mg, 0.62 mmol), Pd2 (dbu)3 (630 mg, 0.21 mmol) and toluene (100 mL) and heat to reflux for 48 hours. Cool the reaction to room temperature, dissolve in ether and filter and concentrate the resulting solution. Purification by flash chromatography (hexanes/EtOAc (8.5:1.5) and then hexanes/EtOAc (7:3)) provides the title compound as a yellow oil.

Workup

  1. temperatureto reflux for 48 hours
  2. temperatureCool
  3. customthe reaction to room temperature
  4. filtrationfilter
  5. concentrationconcentrate the resulting solution
  6. customPurification by flash chromatography (hexanes/EtOAc (8.5:1.5)

Sources & evidence

ORD record
ord-111b326c21d5427196a13845a361fbc9
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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