HCID 90402607, compound → HCID 131736005, compound

HRID 1049360Notes

Reaction equation

HRID 1049360 reaction equation
[CH3:1][N:2]([C:10]1[N:15]=[CH:14][C:13]([C:16]2[CH:21]=[C:20]([O:22][C:23]3[CH:24]=[N:25][C:26]([N+:29]([O-])=O)=[CH:27][CH:28]=3)[CH:19]=[CH:18][N:17]=2)=[CH:12][CH:11]=1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]>CCOC(C)=O.[Pd]>[NH2:29][C:26]1[N:25]=[CH:24][C:23]([O:22][C:20]2[CH:19]=[CH:18][N:17]=[C:16]([C:13]3[CH:14]=[N:15][C:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8])=[CH:11][CH:12]=3)[CH:21]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 1

HCID 90402607HCID 90402607, compound

Product 1

HCID 131736005HCID 131736005, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl methyl(4-((6-nitropyridin-3-yl)oxy)-[2,3′-bipyridin]-6′-yl)carbamate (0.26 g, 0.614 mmol) in EtOAc (10 mL) was treated with 10% Pd/C (50% wet, 6.53 mg, 0.061 mmol) and hydrogenated (1 atm) for 16 h. The solids were removed via filtration through diatomaceous earth, washed with EtOAc and the filtrate concentrated to dryness to afford tert-butyl (4-((6-aminopyridin-3-yl)oxy)-[2,3′-bipyridin]-6′-yl)(methyl)carbamate (210 mg, 87%) as a white amorphous solid. 1H NMR (400 MHz, DMSO-d6): δ 8.99 (d, J=2.5 Hz, 1H), 8.49 (d, J=5.7 Hz, 1H), 8.34 (dd, J=8.8, 2.5 Hz, 1H), 7.84 (d, J=2.9 Hz, 1H), 7.75 (d, J=8.8 Hz, 1H), 7.55 (d, J=2.4 Hz, 1H), 7.31 (dd, J=8.9, 3.0 Hz, 1H), 6.75 (dd, J=5.7, 2.4 Hz, 1H), 6.52 (d, J=8.9 Hz, 1H), 6.03 (s, 2H), 3.33 (s, 3H), 1.47 (s, 9H); MS (ESI) m/z: 394.2 (M+H+).

Workup

  1. customThe solids were removed via filtration through diatomaceous earth
  2. washwashed with EtOAc
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-6dfee32861ca4299852e7fd4888820fe
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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