Water → HCID 131734682, compound

HRID 1772677Notes

Reaction equation

HRID 1772677 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[NH:6][C:7](=[O:13])[N:8]([CH3:12])[S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:22][Si:23]([CH2:26][CH2:27][O:28][CH2:29]Cl)([CH3:25])[CH3:24].O>CN(C=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:29][O:28][CH2:27][CH2:26][Si:23]([CH3:25])([CH3:24])[CH3:22])[C:7](=[O:13])[N:8]([CH3:12])[S:9](=[O:10])(=[O:11])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 117728272HCID 117728272, compound

Product 1

HCID 131734682HCID 131734682, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of compound 42a (616 mg, 2.10 mmol) in DMF (5 mL) was added K2CO3 (1.0 g, 7.2 mmol) and SEM-Cl (563 μL, 3.17 mmol). The resulting mixture was stirred at 75° C. for 4 h, allowed to cool to rt and treated with water (20 mL). The reaction mixture was then extracted with DCM (3×20 mL). The combined DCM layers were dried over Na2SO4, filtered, and concentrated to obtain a residue which was purified by flash column chromatography on silica gel (0-50% EtOAc/hexanes) to obtain compound 42b. 1H-NMR (400 MHz, CDCl3) δ (ppm): 7.99 (d, J=2.0 Hz, 1H), 7.74 (dd, J=9.1, 2.5 Hz, 1H), 7.51 (d, J=9.1 Hz, 1H), 5.42 (s, 2H), 3.71-3.77 (m, 2H), 3.35 (s, 3H), 0.91-0.98 (m, 2H), 0.01 (s, 9H).

Workup

  1. temperatureto cool to rt
  2. extractionThe reaction mixture was then extracted with DCM (3×20 mL)
  3. dry with materialThe combined DCM layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto obtain a residue which
  7. customwas purified by flash column chromatography on silica gel (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a79d9300f8594972bc8d36f2175e1d64
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

Loading…