2-Bromo-4-pyridinecarboxaldehyde → HCID 86680285, compound

HRID 2202579Notes

Reaction equation

HRID 2202579 reaction equation
[CH:1]([O:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:21][C:22]1[CH:27]=[C:26]([CH:28]=O)[CH:25]=[CH:24][N:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.ClCCl>[CH:1]([O:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:28][C:26]2[CH:25]=[CH:24][N:23]=[C:22]([Br:21])[CH:27]=2)[CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 27629912-Bromo-4-pyridinecarboxaldehydeHCID 30175844-BenzhydryloxypiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86585896Sodium bicarbonate water

Product 1

HCID 86680285HCID 86680285, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 904 mg of 4-benzhydryloxypiperidine synthesized in Production Example 1, 6.4 mL of dichloromethane, and 629 mg of 2-bromo-4-pyridinecarbaldehyde was stirred for 50 minutes. Sodium triacetoxyborohydride (1.075 g) was added thereto little by little, and the resulting mixture was stirred for 14 hours. The resulting mixture was diluted with ethyl acetate, and the diluted mixture was thrown into sodium bicarbonate water. The organic layer was collected by separation and washed with a saturated saline solution. The washed organic layer was dried over magnesium sulfate, and the solvent was distilled off. The resulting product was subjected to a silica gel column chromatography (hexane/ethyl acetate (volume ratio)=2:1 to 1:1) to give the title compound (1.027 g).

Workup

  1. stirringlittle by little, and the resulting mixture was stirred for 14 hours
  2. customThe organic layer was collected by separation
  3. washwashed with a saturated saline solution
  4. dry with materialThe washed organic layer was dried over magnesium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-3c072fdd12954a6cac247e1cbcf1af58
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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