Dimethylformamide → HCID 22473225, compound

HRID 2183488Notes

Reaction equation

HRID 2183488 reaction equation
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[CH:9][N:8]=1.CN([CH:26]=[O:27])C.[BH4-].[Na+]>C1COCC1.CO>[Si:16]([O:15][CH2:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:26][OH:27])=[N:8][CH:9]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 4311764Sodium borohydrideHCID 224732142-Bromo-5-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]pyridineHCID 178418339Butyllithium

Product 1

HCID 22473225HCID 22473225, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

BuLi (14.6 ml of a 1.6 M solution in hexanes, 23 mmol) was added to a stirred solution of 2-bromo-5-[2-(tert-butyldimethylsilyloxy)ethyl]pyridine (4.92 g, 15.6 mmol) in THF (100 ml) at −78° C. The resulting pale yellow solution was stirred for 1 h and then DMF (3.6 ml, 46.6 mmol) was added in one portion. The reaction mixture was warmed to room temperature and stirred for 90 min. MeOH (70 ml) was added, followed by NaBH4 (589 mg, 15.6 mmol) and stirring was continued for a further 1 h. The reaction was quenched by cautious addition of NH4Cl (sat. 100 ml) and the organics extracted with EtOAc (3×100 ml). The combined extracts were then washed with H2O (70 ml) and brine (70 ml), dried (MgSO4) and concentrated under reduced pressure. The material was used crude without further purification.

Workup

  1. stirringstirred for 90 min
  2. stirringstirring
  3. waitwas continued for a further 1 h
  4. customThe reaction was quenched by cautious addition of NH4Cl (sat. 100 ml)
  5. extractionthe organics extracted with EtOAc (3×100 ml)
  6. washThe combined extracts were then washed with H2O (70 ml) and brine (70 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customwithout further purification

Sources & evidence

ORD record
ord-f2a75bebe0b34144a5043cfc771f0bda
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

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