2-Naphthalenecarboxaldehyde → 5-bromo-N-(naphthalen-2-ylmethyl)pyrazin-2-amine

HRID 2239962Notes

Reaction equation

HRID 2239962 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.[NH2:13][C:14]1[CH:19]=[N:18][C:17]([Br:20])=[CH:16][N:15]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.C(O)(=O)C.ClCCl>[Br:20][C:17]1[N:18]=[CH:19][C:14]([NH:13][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[N:15][CH:16]=1

Participants

7

Reactant 3

HCID 62012-NaphthalenecarboxaldehydeHCID 5995392-Amino-5-bromopyrazineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 866143075-bromo-N-(naphthalen-2-ylmethyl)pyrazin-2-amineYield 48.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

2-Napthaldehyde (0.6 g, 3.84 mmol) and 2-amino-5-bromopyrazine (0.56 g, 3.201 mmol) were treated with Na(OAc)3BH (1.02 g, 4.802 mmol) in dichloroethane (15.0 mls) and acetic acid (0.5 mls) for 18 hours at room temperature. The mixture was diluted with dichloromethane, washed with 1.0 N NaOH, washed with brine, dried over MgSO4, and concentrated. Chromatography (SiO2, EtOAc:Hex, 1:1) gave 0.49 g 5-bromo-N-(naphthalen-2-ylmethyl)pyrazin-2-amine.

Workup

  1. washwashed with 1.0 N NaOH
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d77187c394054c5797e24623a61103d3
Source dataset
uspto-grants-2010_05
Patent number
US07723345B2

Reaction notes

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