2,6-Dibromopyridine → HCID 54591862, compound

HRID 2276747Notes

Reaction equation

HRID 2276747 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH3:20])([CH3:19])[CH2:17][NH2:18])=[CH:12][CH:11]=1.CCN(C(C)C)C(C)C>C(#N)C>[Br:8][C:4]1[N:3]=[C:2]([NH:18][CH2:17][C:16]([C:13]2[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=2)([CH3:20])[CH3:19])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 122742,6-DibromopyridineHCID 81531DiisopropylethylamineHCID 212510232-(4-Fluorophenyl)-2-methylpropan-1-amine

Product 1

HCID 54591862HCID 54591862, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
137 °C

Procedure

To a 5 mL microwave reaction vial was added 2,6-dibromopyridine (1.25 g, 5.0 mmol, 1.0 equiv), 2-(4-fluorophenyl)-2-methylpropan-1-amine (1.06 g, 6 mmol, 1.2 equiv), DIPEA (1.9 mL, 11.0 mmol, 2.2 equiv), and acetonitrile (5 mL). The vial was sealed and heated in an oil bath at 137° C. for 48 h, concentrated, and purified by silica gel column chromatography to give 220 mg (14%) of 6-bromo-N-(2-(4-fluorophenyl)-2-methylpropyl)pyridin-2-amine as a white solid (m/z [M+H]=323).

Workup

  1. customTo a 5 mL microwave reaction
  2. customThe vial was sealed
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-b3d63b7af1fe417b8cdce47bb122f718
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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