3-Aminopyridine → HCID 66648256, compound

HRID 417935Notes

Reaction equation

HRID 417935 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][N:7]([C:11]3[S:12][C:13]4[C:19](=[O:20])[CH2:18][C:17]([CH3:22])([CH3:21])[CH2:16][C:14]=4[N:15]=3)[C:6]=2[CH:23]=1.[NH2:24][C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1.CC(C)([O-])C.[Na+]>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:21][C:17]1([CH3:22])[CH2:16][C:14]2[N:15]=[C:11]([N:7]3[C:6]4[CH:23]=[C:2]([NH:24][C:25]5[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=5)[CH:3]=[CH:4][C:5]=4[O:10][CH2:9][CH2:8]3)[S:12][C:13]=2[C:19](=[O:20])[CH2:18]1

Participants

6

Reactant 3

HCID 100093-AminopyridineHCID 23676156Sodium t-butoxideHCID 24955799HCID 24955799, compound

Product 1

HCID 66648256HCID 66648256, compoundYield 8.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 7 (50 mg, 0.14 mmol), 3-aminopyridine (0.171 g, 1.8 mmol), sodium tert-butoxide (0.041 g, 0.43 mmol), palladium(II) acetate (0.158 g, 0.70 mmol) and (But)3PBF4 (0.225 g, 0.78 mmol) in THF (3 mL) was heated to 140° C. under microwave irradiation for 80 min. After cooling to r.t., the mixture was concentrated in vacuo. The crude material was purified by prep HPLC to give the title compound as an off-white solid (5 mg, 8.7%). δH (CDCl3) 1.16 (6H, s), 2.44 (2H, s), 2.78 (2H, s), 4.12-4.22 (2H, m), 4.31-4.41 (2H, m), 5.75 (1H, br s), 6.84-6.89 (1H, m), 6.92-6.96 (1H, m), 7.20 (1H, dd, J 8.7, 5.1 Hz), 7.37-7.44 (1H, m), 7.87 (1H, d, J 2.6 Hz), 8.14 (1H, d, J 4.7 Hz), 8.33 (1H, d, J 2.8 Hz). LCMS (ES+) 407.0 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe crude material was purified by prep HPLC

Sources & evidence

ORD record
ord-d97a034f74d849c68994b0ce9dbc619b
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

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