HCID 58361484, compound → HCID 58361491, compound

HRID 2076449Notes

Reaction equation

HRID 2076449 reaction equation
[C:1]1([S:7]([O:10][C:11]2[C:20]([Br:21])=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([CH:22]([OH:26])[CH2:23][C:24]#[N:25])=[N:18]3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1>[C:1]1([S:7]([O:10][C:11]2[C:20]([Br:21])=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([CH:22]([OH:26])[CH2:23][CH2:24][NH2:25])=[N:18]3)=[CH:13][CH:12]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 58361484HCID 58361484, compound

Product 1

HCID 58361491HCID 58361491, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 8-Bromo-2-(2-cyano-1-hydroxyethyl)quinolin-7-yl benzenesulfonate (890 mg, 2.05 mmol) in THF (2 mL) were slowly added 1 M BH3-THF complex (4.1 mL, 4.10 mmol) at 0° C. And the reaction mixture was slowly warmed to room temperature. The mixture was then refluxed for 1 h, then cooled to 0° C. and quenched with MeOH. After the removal of solvents in vacuo, the mixture was stirred with 1.2N HCl in MeOH for 10 min. After the removal of solvents in vacuo again, the residue was dissolved in CHCl3 extracted with and washed twice with saturated aq. NaHCO3 and then dried over anhydrous Na2SO4. Solvent was removed in vacuo to yield 895 mg SO190 as a yellow oil and was used for next step without further purification.

Workup

  1. customat 0° C
  2. temperatureThe mixture was then refluxed for 1 h
  3. temperaturecooled to 0° C.
  4. customquenched with MeOH
  5. customAfter the removal of solvents in vacuo
  6. customAfter the removal of solvents in vacuo again
  7. dissolutionthe residue was dissolved in CHCl3
  8. extractionextracted with and
  9. washwashed twice with saturated aq. NaHCO3
  10. dry with materialdried over anhydrous Na2SO4
  11. customSolvent was removed in vacuo
  12. customto yield 895 mg SO190 as a yellow oil
  13. customwas used for next step without further purification

Sources & evidence

ORD record
ord-74858315e87c455b8ef6338d7f9e7ff1
Source dataset
uspto-grants-2011_04
Patent number
US07923562B2

Reaction notes

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