Iodoethane → HCID 86699803, compound

HRID 879285Notes

Reaction equation

HRID 879285 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]3[C:16]([C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=4)=[C:15]([C@H:24]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:25]([OH:27])=[O:26])[C:14]([CH3:33])=[CH:13][C:11]=3[N:12]=2)[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:40](I)[CH3:41]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]3[C:16]([C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=4)=[C:15]([C@H:24]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])[C:25]([O:27][CH2:40][CH3:41])=[O:26])[C:14]([CH3:33])=[CH:13][C:11]=3[N:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 86699804HCID 86699804, compound

Product 1

HCID 86699803HCID 86699803, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-2-(2-(3-bromophenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetic acid (104 mg, 0.191 mmol) in DMF, was added Cs2CO3 (152 mg, 0.467 mmol), ethyl iodide (30 μL, 0.343 mmol). The reaction was stirred at room temperature for 2hs. The reaction mixture was washed by sat. NaHCO3, extracted by EtOAc, dry over MgSO4, filtered, purified by silica gel column, eluting by 0-50% EtOAc in hexanes to give the product. LCMS-ESI+: calc'd for C28H27BrClNO3S: 572.1 (M+H+); Found: 572.2 (M+H+).

Workup

  1. washThe reaction mixture was washed by sat. NaHCO3
  2. extractionextracted by EtOAc
  3. dry with materialdry over MgSO4
  4. filtrationfiltered
  5. custompurified by silica gel column
  6. washeluting by 0-50% EtOAc in hexanes
  7. customto give the product

Sources & evidence

ORD record
ord-3285c69d60a446a9b4ef4397a04f3e47
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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