Triphenylphosphine → 4-(2-(4-Nitronaphthalen-1-yloxy)ethyl)pyridin-3-amine

HRID 2069032Notes

Reaction equation

HRID 2069032 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[NH2:34][C:35]1[CH:36]=[N:37][CH:38]=[CH:39][C:40]=1[CH2:41][CH2:42]O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:42][CH2:41][C:40]2[CH:39]=[CH:38][N:37]=[CH:36][C:35]=2[NH2:34])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 3438294-Nitro-1-naphtholHCID 5363146Diisopropyl azodicarboxylateHCID 468355964-Pyridineethanol, 3-amino-

Product 1

HCID 584167784-(2-(4-Nitronaphthalen-1-yloxy)ethyl)pyridin-3-amineYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-nitronaphthol (2) (0.95 g, 5.00 mmol), PPh3 (1.97 g, 7.50 mmol) and 2-(3-aminopyridin-4-yl)ethanol (25) (1.04 g, 7.50 mmol) in THF (20 mL) was added dropwise DIAD (590 μL, 3.75 mmol) at −15° C. The mixture was stirred for 1 hr at RT and the volatiles removed in vacuo. The residues was absorbed on silica (20 g) and purified by column chromatography (SiO2, 80 g, 50-100% EtOAc in isohexane, gradient elution and then 5% MeOH in EtOAc, isocratic elution) to give the title compound (26) (1.36 g, 88%): m/z 310 (M+H)+ (ES+).

Workup

  1. customthe volatiles removed in vacuo
  2. customThe residues was absorbed on silica (20 g)
  3. custompurified by column chromatography (
  4. washSiO2, 80 g, 50-100% EtOAc in isohexane, gradient elution
  5. wash5% MeOH in EtOAc, isocratic elution)

Sources & evidence

ORD record
ord-4f13b8ddaf364bff90486f31e23ab3f7
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

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