HCID 59857443, compound → HCID 28890094, compound

HRID 555417Notes

Reaction equation

HRID 555417 reaction equation
[C:1]([C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=1[O:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N+:14]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>CO.C(OCC)(=O)C.[Pd]>[C:1]([C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=1[O:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[NH2:14])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 59857443HCID 59857443, compound

Product 1

HCID 28890094HCID 28890094, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

137a (1.332 g, 4.891 mmol) was dissolved in a 111 mixture of methanol and ethyl acetate (30 mL). Palladium on charcoal (10%, 200 mg, 0.188 mmol) was added, and the mixture was stirred 2 h under hydrogen atmosphere (40 psi). The reaction mixture was filtered over Celite® and concentrated to afford 1.16 g (98% yield, 100% pure) of 4-(2-tert-butylphenoxy)pyridin-3-amine (137b) as a white solid. [M+H]+=243.17. 1H NMR (500 MHz, deuterochloroform) δ ppm 8.07 (s, 1H), 7.75 (d, 1H, J=5.0 Hz), 7.32 (d, 1H, J=10.0 Hz), 7.03 (m, 2H), 6.77 (d, 1H, J=5.0 Hz), 6.41 (d, 1H, J=5.0 Hz), 4.26 (br, 2H), 1.27 (s, 9H); 13C (125 MHz, deuterochloroform) δ (ppm), 152.89, 150.65, 140.96, 139.93, 137.42, 134.21, 127.13, 126.93, 124.22, 120.56, 110.45, 34.19, 29.86.

Workup

  1. filtrationThe reaction mixture was filtered over Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0452ab67e976406298c1de6ea62b661d
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

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