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

HRID 559103Notes

Reaction equation

HRID 559103 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-11c101af45ff42d6bb1937cd024dc037
Source dataset
uspto-grants-2011_11
Patent number
US08063057B2

Reaction notes

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