2-Chloropyridine → N-(4-(3-Bromopyridin-2-yloxy)phenyl)pyridin-2-amine hydrochloride

HRID 473627Notes

Reaction equation

HRID 473627 reaction equation
[Br:1][C:2]1[C:3]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1>CCOCC>[ClH:16].[Br:1][C:2]1[C:3]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH:13][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 79772-ChloropyridineHCID 577562564-(3-Bromopyridin-2-yloxy)benzenamine

Product 1

HCID 67425919N-(4-(3-Bromopyridin-2-yloxy)phenyl)pyridin-2-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 4-(3-bromopyridin-2-yloxy)aniline (50.01 g, 188.6 mmol) and 2-chloropyridine (22.50 ml, 238.8 mmol, Aldrich) was sealed neat in a 350 mL screw-cap flask and heated at 160° C. for 3.5 h. The reaction was cooled to room temperature and stirred over Et2O overnight. The solid was filtered, washed with Et2O and dried in vacuo to give a gray amorphous solid. MS (ESI, pos. ion) m/z: 341.9, 343.9 [M+1]. PDE10 IC50 (uM) 0.96.

Workup

  1. customwas sealed neat in a 350 mL
  2. customscrew-cap flask
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationThe solid was filtered
  5. washwashed with Et2O
  6. customdried in vacuo
  7. customto give a gray amorphous solid

Sources & evidence

ORD record
ord-8324fa2eac054867abca2f3652f02989
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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