HCID 71007327, compound → HCID 71007334, compound

HRID 716188Notes

Reaction equation

HRID 716188 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-])=O)[CH:7]=1>CCO.CCOC(C)=O.[Pd]>[NH2:14][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[C:6]1[CH:5]=[C:4]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 1

HCID 71007327HCID 71007327, compound

Product 1

HCID 71007334HCID 71007334, compoundYield 111.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-butyl (3-(3-aminopyridin-4-yl)-5-methylphenyl) carbamate. A solution of tert-butyl (3-methyl-5-(3-nitropyridin-4-yl)phenyl)carbamate (198 mg, 0.60 mmol) in EtOH (5 mL) and EtOAc (5 mL) was degassed by bubbling N2 (g) through the solution for 10 min. Pd/C (10 wt %, 64 mg, 0.060 mmol) was added. A gas bag with a 3-way stopcock filled with H2 was attached to the flask. The flask was evacuated under vacuum and then back-filled with H2 (3×). The mixture was stiffed overnight at RT. The solution was degassed by bubbling N2 (g) through the solution for 10 min and was then filtered through celite. The solution was concentrated to afford tert-butyl (3-(3-aminopyridin-4-yl)-5-methylphenyl)carbamate (200 mg, 0.67 mmol, 111% yield) as an off-white foam. MS (ESI, pos. ion) m/z: 300.0 (M+1).

Workup

  1. customby bubbling N2 (g) through the solution for 10 min
  2. additionA gas bag with a 3-way stopcock filled with H2
  3. customThe flask was evacuated under vacuum
  4. additionback-filled with H2 (3×)
  5. customThe solution was degassed
  6. customby bubbling N2 (g) through the solution for 10 min
  7. filtrationwas then filtered through celite
  8. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-886ab991c7fe4d059be079548838d921
Source dataset
uspto-grants-2015_11
Patent number
US09187486B2

Reaction notes

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