Water → HCID 66695588, compound

HRID 330817

Reaction equation

HRID 330817 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C1COCC1>[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 104392-AminopyridineHCID 966574-IodobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 66695588HCID 66695588, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

2.00 g (8.62 mmol) 4-iodo-benzaldehyde are added to 0.811 g (8.62 mmol) 2-amino-pyridine in 20 mL THF and the mixture is stirred for 1 h at 50° C. After that time, 4.57 g (21.5 mmol) sodium triacetoxyborohydride are added and the mixture is stirred for 1 h at 50° C. Subsequently, water is added and the mixture is extracted with EtOAc. The organic layer is dried over magnesium sulphate and the solvent is removed in vacuo. The residue is purified by RP-HPLC to yield the desired product.

Workup

  1. stirringthe mixture is stirred for 1 h at 50° C
  2. extractionthe mixture is extracted with EtOAc
  3. dry with materialThe organic layer is dried over magnesium sulphate
  4. customthe solvent is removed in vacuo
  5. customThe residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-ecc78df6dcc44bd7944d672c422118ab
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Linked notes

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