Cesium carbonate → HCID 21084058, compound

HRID 347917Notes

Reaction equation

HRID 347917 reaction equation
Br[CH2:2][CH2:3][OH:4].[OH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]3[C:19]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[S:21][C:13]2=3)=[CH:8][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[OH:4][CH2:3][CH2:2][O:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[C:17](=[O:18])[CH:16]=[CH:15][C:14]3[C:19]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[S:21][C:13]2=3)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 21084070HCID 21084070, compound

Product 1

HCID 21084058HCID 21084058, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromoethanol (0.148 mL, 2.08 mmol) was added to the compound of Example 89 (370 mg, 0.95 mmol) and Cs2CO3 (342 mg, 1.04 mmol) in DMF (5 mL) and the mixture heated at 80° for 2 days. The solvent was removed in vacuo and the residue partitioned between EtOAc and HCl (10%). The aqueous phase was extracted with EtOAc (2×20 mL). The combined organics were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by column chromatography on silica (2% to 10% MeOH in DCM) to give the title compound (73 mg, 18%). δH (CDCl3) 7.44–7.28 (8H, m), 7.07 (2H, d, J 8 Hz), 6.52 (1H, d, J 9.6 Hz), 4.12–3.93 (6H, m), 1.06 (3H, t, J 7.1 Hz). LCMS (ES+) RT 3.42 minutes, 436 (M+H)+.

Workup

  1. temperaturethe mixture heated at 80° for 2 days
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between EtOAc and HCl (10%)
  4. extractionThe aqueous phase was extracted with EtOAc (2×20 mL)
  5. washThe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography on silica (2% to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-d63f28bed48846dc9fe2aaa5fee7b358
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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