Sodium hydride → HCID 59717607, compound

HRID 2224368Notes

Reaction equation

HRID 2224368 reaction equation
[CH:1]([C:3]1[C:4]([NH:9][C:10](=[O:12])[CH3:11])=[N:5][CH:6]=[CH:7][CH:8]=1)=[CH2:2].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[C:16]([CH2:21]Br)[CH:15]=1.[H-].[Na+]>CN(C=O)C.C([O-])(O)=O.[Na+]>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([I:20])=[C:16]([CH:15]=1)[CH2:21][N:9]([C:4]1[C:3]([CH:1]=[CH2:2])=[CH:8][CH:7]=[CH:6][N:5]=1)[C:10](=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 110033124-Bromo-2-(bromomethyl)-1-iodobenzeneHCID 21702077HCID 21702077, compound

Product 1

HCID 59717607HCID 59717607, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of N-(3-Vinyl-pyridin-2-yl)-acetamide 78D (122 mg, 0.75 mmol) and 4-Bromo-2-bromomethyl-1-iodo-benzene (285 mg, 0.75 mmol) in anhydrous DMF (6 mL) under argon was added 95% NaH (21 mg, 0.83 mmol). This mixture was stirred at room temperature for 4.5 h and diluted with saturated NaHCO3 solution. This was extracted with EtOAc (4×60 mL). The combined EtOAc extracts were washed with brine (30 mL), dried (MgSO4), filtered and concentrated in vacuo. This was purified by a ISCO auto CombiFlash with a RediSep 10 g column, eluted with CH2Cl2-EtOAc, detected at 220 nM to give 90 mg of desired N-(5-Bromo-2-iodo-benzyl)-N-(3-vinyl-pyridin-2-yl)-acetamide 78E in 29% yield. HPLC Rt=3.48 min (YMC S5 ODS column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm) LC/MS: M+H=457.

Workup

  1. extractionThis was extracted with EtOAc (4×60 mL)
  2. washThe combined EtOAc extracts were washed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThis was purified by a ISCO auto CombiFlash with a RediSep 10 g column
  7. washeluted with CH2Cl2-EtOAc

Sources & evidence

ORD record
ord-5867fd1e9f8245f6b8419c722f46c640
Source dataset
uspto-grants-2008_05
Patent number
US07378426B2

Reaction notes

Loading…