(1,1'-Biphenyl)-4-carboxaldehyde → N-(biphenyl-4-ylmethyl)-5-bromopyrazin-2-amine

HRID 419247Notes

Reaction equation

HRID 419247 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:15][C:16]1[CH:21]=[N:20][C:19]([Br:22])=[CH:18][N:17]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.C(O)(=O)C.ClCCl>[C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:14]=[CH:13][C:10]([CH2:11][NH:15][C:16]2[CH:21]=[N:20][C:19]([Br:22])=[CH:18][N:17]=2)=[CH:9][CH:8]=1

Participants

7

Reactant 3

HCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 5995392-Amino-5-bromopyrazineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 86614306N-(biphenyl-4-ylmethyl)-5-bromopyrazin-2-amineYield 38.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

4-Phenylbenzaldehyde (0.3 g, 1.65 mmol) and 2-amino-5-bromopyrazine (0.24 g, 1.37 mmol) were treated with Na(OAc)3BH (0.44 g, 2.06 mmol) in dichloroethane (7.0 mls) and acetic acid (0.25 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 0.18 g of N-(biphenyl-4-ylmethyl)-5-bromopyrazin-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-9bf4b08fc8d1401a8637b747d5be7c1e
Source dataset
uspto-grants-2012_01
Patent number
US08093291B2

Reaction notes

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