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

HRID 469873
Notes
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Reaction equation

HRID 469873 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 AcidSolvent
HCID 6344
Dichloromethane
Solvent
HCID 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-719929ee8809478ca8284915f2a40447
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08629156B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes