Cesium carbonate → HCID 59282914, compound

HRID 1879563Notes

Reaction equation

HRID 1879563 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+].BrCC[F:32]>CN(C=O)C.O.C(O)(=O)C.[Pd]>[F:32][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 129822-Fluoroethyl bromideHCID 17834913HCID 17834913, compound

Product 1

HCID 59282914HCID 59282914, compoundYield 31.2%

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 (62 mg, 0.19 mmol) and 1-bromo-2-fluoroethane (33 mg, 0.26 mmol). The reaction was stirred at rt for 15 h and then diluted with water (15 mL). White precipitate (50 mg) was collected via filtration and dried in vacu. The solid was dissolved in MeOH (10 mL). To the reaction, was added Pd/C (30 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, concentrated in vacuo. The residue was purified on HPLC to afford CB-25 (18 mg, 0.053 mmol, 31% yield). 1H NMR (400 MHz, CD3CN) δ: 8.99 (br, 1H), 7.72 (d, J=8.4 Hz, 1H), 7.67 (d, J=8.4 Hz, 1H), 6.88 (d, J=2.0 Hz, 1H), 6.76 (d, J=2.0 Hz, 1H), 6.67 (dd, J=8.0 Hz, 2.0 Hz, 1H), 6.58 (dd, J=8.0 Hz, 2.0 Hz, 1H), 4.75-4.74 (m, 1H), 4.63-4.61 (m, 1H), 4.23-4.13 (m, 2H); LRMS for C16H12F4NO3+H+, calc'd: 343.1. found: 246.0 (M+H+-TFA).

Workup

  1. filtrationWhite precipitate (50 mg) was collected via filtration
  2. customdried in vacu
  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

Sources & evidence

ORD record
ord-4c7ef43bbb6744eb8281cf3161eae94c
Source dataset
uspto-grants-2012_11
Patent number
US08318132B2

Reaction notes

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