Ammonium cerium (IV) nitrate → 4-(4-Amino-3-fluorophenoxy)pyridin-2-amine

HRID 2042075Notes

Reaction equation

HRID 2042075 reaction equation
COC1C=CC(C[NH:8][C:9]2[CH:14]=[C:13]([O:15][C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([F:23])[CH:17]=3)[CH:12]=[CH:11][N:10]=2)=CC=1.[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>C(Cl)Cl>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:13]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:8])[CH:14]=2)=[CH:17][C:18]=1[F:23]

Participants

4

Reactant 2

HCID 9869224Ammonium cerium (IV) nitrateHCID 66605351N-(4-methoxybenzyl)-4-(4-amino-3-fluorophenoxy)pyridin-2-amine

Product 1

HCID 71470884-(4-Amino-3-fluorophenoxy)pyridin-2-amineYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(4-methoxybenzyl)-4-(4-amino-3-fluorophenoxy)pyridin-2-amine (500 mg, 1.47 mmol) in CH2Cl2 (10 mL) was treated with ammonium cerium(IV) nitrate (1.64 g, 2.99 mmol) and the resultant mixture was stirred at RT overnight. The reaction mixture was washed with water, concentrated in vacuo and purified by silica gel chromatography to yield 4-(4-amino-3-fluorophenoxy)pyridin-2-amine (250 mg, 77% yield). 1H NMR (300 MHz, DMSO-d6) δ 7.73 (d, J=6.0 Hz, 1H), 6.88 (dd, J=9.0, 2.0 Hz, 1H), 6.80 (t, J=8.7 Hz, 1H), 6.68 (m, 1H), 6.06 (dd, J=4.5, 1.8 Hz, 1H), 5.84 (s, 2H), 5.75 (d, J=1.5 Hz, 1H), 5.08 (s, 2H); MS (ESI) m/z: 220.3 (M+H+).

Workup

  1. washThe reaction mixture was washed with water
  2. concentrationconcentrated in vacuo
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-6a343b8222694f5ca685b76beaed65e2
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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