Cesium carbonate → HCID 59283053, compound

HRID 1425583Notes

Reaction equation

HRID 1425583 reaction equation
[CH2:1]([O:8][C:9]1[CH:21]=[C:20]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([OH:22])=[CH:17][C:18]=3[NH:19]2)=[CH:11][CH:10]=1)[C:2]1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1C=CC(S(OCC[O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47][F:48])(=O)=O)=CC=1>CN(C=O)C.O.C(O)(=O)C.[Pd]>[F:48][CH2:47][CH2:46][O:45][CH2:44][CH2:43][O:42][CH2:2][CH2:1][O:8][C:9]1[CH:21]=[C:20]2[C:12]([C:13]3[CH:14]=[CH:15][C:16]([OH:22])=[CH:17][C:18]=3[NH:19]2)=[CH:11][CH:10]=1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 17834913HCID 17834913, compoundHCID 595523472-[2-(2-Fluoroethoxy)ethoxy]ethyl 4-methylbenzene-1-sulfonate

Product 1

HCID 59283053HCID 59283053, compoundYield 27%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a round bottom flask containing Compound 8 (50 mg, 0.17 mmol) in DMF (1 ml), was added cesium carbonate (56 mg, 0.17 mmol) and 2-(2-(2-fluoroethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (53 mg, 0.17 mmol). The reaction was stirred at rt for 15 h and then diluted with water (15 mL). White precipitate (72 mg) was collected via filtration and dried in vacou. The solid was dissolved in MeOH (10 mL). To the reaction, was added Pd/C (20 mg) and acetic acid (5 drops). The mixture was stirred under hydrogen (1 atm) atmosphere for 20 h and then filtered through a celite plug and concentrated in vacuo. The residue was purified on HPLC to afford CB-26 (20 mg, 0.046 mmol, 27% yield). 1H NMR (400 MHz, CD3CN) δ: 9.03 (br, 1H), 7.81-7.75 (m, 2H), 6.96 (d, J=2.4 Hz, 1H), 6.84 (d, J=2.4 Hz, 1H), 6.76 (dd, J=7.6 Hz, 2.0 Hz, 1H), 6.67 (dd, J=7.6 Hz, 2.0 Hz, 1H), 4.59-4.57 (m, 1H), 4.47-4.45 (m, 1H), 4.17-4.15 (m, 2H), 3.83-3.63 (m, 8H); LRMS for C20H20NO5+H+, calc'd: 431.1. found: 334.1 (M+H+-TFA).

Workup

  1. filtrationWhite precipitate (72 mg) was collected via filtration
  2. customdried in vacou
  3. dissolutionThe solid was dissolved in MeOH (10 mL)
  4. customTo the reaction
  5. stirringThe mixture was stirred under hydrogen (1 atm) atmosphere for 20 h
  6. filtrationfiltered through a celite plug
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified on HPLC
  9. customto afford CB-26 (20 mg, 0.046 mmol, 27% yield)

Sources & evidence

ORD record
ord-45de32e6cb4a4f9caa2e58ee2865cda8
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

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