Isopropyl iodide → HCID 71237857, compound

HRID 1496867Notes

Reaction equation

HRID 1496867 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[CH:13][CH:14]=[N:15]3)=[C:10]([O:18][CH2:19][C@@H:20]3[O:24][C:23](=[O:25])[NH:22][CH2:21]3)[CH:9]=2)=[CH:4][C:3]=1[O:26][CH3:27].I[CH:29]([CH3:31])[CH3:30].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C>[CH:29]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[C:16]3[C:11]([CH:12]=[CH:13][CH:14]=[N:15]3)=[C:10]([O:18][CH2:19][C@@H:20]3[O:24][C:23](=[O:25])[NH:22][CH2:21]3)[CH:9]=2)=[CH:4][C:3]=1[O:26][CH3:27])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 6362Isopropyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 136263954HCID 136263954, compound

Product 1

HCID 71237857HCID 71237857, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 59 mg (R)-5-[7-(4-hydroxy-3-methoxy-phenyl)-quinolin-5-yloxymethyl]-oxazolidin-2-one (Example 13), 19.3 μl 2-iodopropane and 44 mg potassium carbonate in DMF (10 ml) was stirred at 50° C. for 16 hours. The mixture was poured into EtOAc and washed with water then brine and dried over Na2SO4. Purification by FCC over SiO2, eluting with EtOAc-MeOH from 100:0 to 95:5 yielded 56 mg (85%) of (R)-5-[7-(4-Isopropoxy-3-methoxy-phenyl)-quinolin-5-yloxymethyl]-oxazolidin-2-one (Example 16) as an oily residue.

Workup

  1. washwashed with water
  2. dry with materialbrine and dried over Na2SO4
  3. customPurification by FCC over SiO2
  4. washeluting with EtOAc-MeOH from 100:0 to 95:5

Sources & evidence

ORD record
ord-7e2fcf772af74ca6af6882b87fbfb388
Source dataset
uspto-grants-2015_12
Patent number
US09199937B2

Reaction notes

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