Dichloromethane → HCID 11775958, compound

HRID 1611701Notes

Reaction equation

HRID 1611701 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5](S(C(F)(F)F)(=O)=O)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(Cl)Cl>C1COCC1>[CH2:8]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([NH2:1])[CH:11]=[CH:10]2)[CH2:9][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 22254628HCID 22254628, compound

Product 1

HCID 11775958HCID 11775958, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-amino-8-trifluoromethanesulfonylquinoline (50.0 mg, 0.171 mmol) in THF (1.0 mL) was degassed by bubbling N2 through the solution under vacuum for 5 min. The solution was added to a glass screw-top tube containing Pd(dppf)2Cl2.CH2Cl2 (13.9 mg, 0.1 equiv). Argon was then bubbled through the mixture for 1 minute, and 1-hexylzinc bromide (1.0 mL, 1 M in THF) was added. The tube was quickly sealed and placed in a heater/shaker at 65° C. for 20 h. The reaction mixture was cooled to room temperature, filtered through a 0.45 μm filter, and concentrated. The residue was dissolved in 1:1 DMSO/MeOH, filtered through a 0.45 μm filter, and purified by reverse phase HPLC. 1H NMR (300 MHz, DMSO-d6) δ 9.10 (br s, 1H), 8.36 (br s, 1H), 8.23 (br s, 1H), 7.77 (d, 1H), 7.63 (d, 1H), 7.43 (br s, 1H), 7.10 (d, 1H), 1.41–1.25 (m, 10H), 0.86 (t, 3H); MS (DCI/NH3) m/z 228 [M]+.

Workup

  1. customby bubbling N2 through the solution under vacuum for 5 min
  2. additionThe solution was added to a glass screw-top tube
  3. additioncontaining Pd(dppf)2Cl2
  4. customArgon was then bubbled through the mixture for 1 minute
  5. addition1-hexylzinc bromide (1.0 mL, 1 M in THF) was added
  6. customThe tube was quickly sealed
  7. filtrationfiltered through a 0.45 μm
  8. filtrationfilter
  9. concentrationconcentrated
  10. dissolutionThe residue was dissolved in 1:1 DMSO/MeOH
  11. filtrationfiltered through a 0.45 μm
  12. filtrationfilter
  13. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-f27f57a0d1cf4ed88a243ca912a361e4
Source dataset
uspto-grants-2006_01
Patent number
US06989392B2

Reaction notes

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