Sodium hydride → HCID 58431001, compound

HRID 1040438Notes

Reaction equation

HRID 1040438 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1.[H-].[Na+]>>[Br:1][C:2]1[N:7]=[C:6]([N:8]([CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[CH2:15][C:14]2[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 58431001HCID 58431001, compoundYield 106.7%

Procedure

To a solution of 6-bromo-pyridin-2-ylamine (1.00 g, 5.78 mmol) under a nitrogen atmosphere at room temperature was added 4-methoxybenzyl chloride (1.96 mL, 14.5 mmol) in one portion. To this mixture was added NaH (60% suspension in mineral oil, 694 mg, 17.3 mmol) in one portion. The reaction was stirred for 2 h then partitioned between aqueous NaHCO3 and CH2Cl2. The layers were separated and the aqueous layer was further extracted with CH2Cl2. The combined organic layers were dried with MgSO4 and concentrated in vacuo to give a light yellow oil. This oil was purified by flash chromatography on silica gel (1→15% EtOAc/hexanes) to give 2.55 g of the title compound as a colorless oil, m/z 413.9 [M−H]+.

Workup

  1. customthen partitioned between aqueous NaHCO3 and CH2Cl2
  2. customThe layers were separated
  3. extractionthe aqueous layer was further extracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give a light yellow oil
  7. customThis oil was purified by flash chromatography on silica gel (1→15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d1de950e8b664f8080161b15cfc77f11
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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