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

HRID 1711655Notes

Reaction equation

HRID 1711655 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-ff801fccb6ed4b309e0c5b4e9a5ce52f
Source dataset
uspto-grants-2010_09
Patent number
US07790756B2

Reaction notes

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