Formaldehyde → HCID 86729282, compound

HRID 1399885Notes

Reaction equation

HRID 1399885 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[C:9]3[CH:10]=[C:11]([Br:14])[CH:12]=[CH:13][C:8]=3[N:7]=[CH:6]2)[CH2:2]1.C=O.[BH3-][C:18]#N.[Na+]>CO.CC(O)=O>[Br:14][C:11]1[CH:12]=[CH:13][C:8]2[N:7]=[CH:6][N:5]([CH:3]3[CH2:4][N:1]([CH3:18])[CH2:2]3)[C:9]=2[CH:10]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86729275HCID 86729275, compound

Product 1

HCID 86729282HCID 86729282, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(azetidin-3-yl)-6-bromo-1H-benzo[d]imidazole (100 mg, 0.396 mmol) in MeOH (10 mL) was added HCHO (300 mg, 3.96 mmol) and AcOH (two drops). The reaction mixture was stirred at room temperature for 30 min. NaCNBH3 (29.7 mg, 0.476 mmol) was then added and the reaction mixture stirred at room temperature for 2 h. The solvents were then removed by concentration and the residue was used for next step without purification. ESI-MS (m/z): 266.1 [M+1]

Workup

  1. stirringthe reaction mixture stirred at room temperature for 2 h
  2. customThe solvents were then removed by concentration
  3. customthe residue was used for next step without purification

Sources & evidence

ORD record
ord-a11693ad6e6a4ff2866892a725bff228
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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