(4-Methoxyphenyl)boronic acid → 5-Bromo-N-(4-methoxyphenyl)pyrazin-2-amine

HRID 1915028

Reaction equation

HRID 1915028 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[Br:12][C:13]1[N:14]=[CH:15][C:16]([NH2:19])=[N:17][CH:18]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:12][C:13]1[N:14]=[CH:15][C:16]([NH:19][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:17][CH:18]=1

Participants

5

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 5995392-Amino-5-bromopyrazine

Product 1

HCID 534150715-Bromo-N-(4-methoxyphenyl)pyrazin-2-amineYield 10.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Into a 50 mL roundbottom flask, was placed 4-methoxyphenylboronic acid (5.4 g, 35.54 mmol). To this was added 5-bromo-pyrazin-2-ylamine (3 g, 17.24 mmol). Cu(OaC)2 (3.45 g, 19.06 mmol) was added, followed by addition of a solution of DMAP (4.2 g, 34.43 mmol) in CH2Cl2 (20 mL). The resulting solution was stirred at room temperature for 12 hours. The reaction progress was monitored by thin layer chromatography (TLC) (ethyl acetate/petroleum ether=1:2). When the reaction was complete, the mixture was filtered, then concentrated under vacuum. The residue was dissolved in ethyl acetate (EtOAc), then washed with water. The organic layer was dried over Na2SO4, then filtered and concentrated. The crude product was purified by silica gel chromatography (SGC) eluting with ethyl acetate/petroleum ether (1:5, v/v) to provide (5-bromo-pyrazin-2-yl)-(4-methoxy-phenyl)-amine (i) (500 mg, yield 10%) as a yellow solid.

Workup

  1. customInto a 50 mL roundbottom flask, was placed
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was dissolved in ethyl acetate (EtOAc)
  5. washwashed with water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel chromatography (SGC)
  10. washeluting with ethyl acetate/petroleum ether (1:5

Sources & evidence

ORD record
ord-0020134caac8437ebf63ccc4b209b20c
Source dataset
uspto-grants-2013_12
Patent number
US08614321B2

Linked notes

Loading…