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4-Toluenesulfonyl chloride → (R)-2-(5-bromo-7-methylquinolin-6-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

HRID 2207044
Notes
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Reaction equation

HRID 2207044 reaction equation
[Br:1][C:2]1[C:11]([C@@H:12]([OH:15])[CH2:13][OH:14])=[C:10]([CH3:16])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([Sn](=O)CCCC)CCC.[S:27](Cl)([C:30]1[CH:36]=[CH:35][C:33]([CH3:34])=[CH:32][CH:31]=1)(=[O:29])=[O:28].CCN(CC)CC>C(Cl)Cl>[CH3:34][C:33]1[CH:35]=[CH:36][C:30]([S:27]([O:14][CH2:13][C@@H:12]([C:11]2[C:2]([Br:1])=[C:3]3[C:8](=[CH:9][C:10]=2[CH3:16])[N:7]=[CH:6][CH:5]=[CH:4]3)[OH:15])(=[O:29])=[O:28])=[CH:31][CH:32]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 61221Dibutyltin oxideHCID 89676590(R)-1-(5-bromo-7-methylquinolin-6-yl)ethane-1,2-diol

Product 1

HCID 89676717(R)-2-(5-bromo-7-methylquinolin-6-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a stirred solution of (R)-1-(5-bromo-7-methylquinolin-6-yl)ethane-1,2-diol (197 mg, 0.70 mmol) in CH2Cl2 (97 mL), dibutyltinoxide (3.3 mg, 0.01 mmol), TsCl (150 mg, 0.79 mmol), and Et3N (0.12 mL, 0.83 mmol) were added at 0° C. The reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was quenched with saturated aqueous NH4Cl, and then diluted with CH2Cl2. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 5 to 100% ethyl acetate/hexanes) to give (R)-2-(5-bromo-7-methylquinolin-6-yl)-2-hydroxyethyl 4-methylbenzenesulfonate. LCMS-ESI+ (m/z): [M+H]+ calc'd for C19H19BrNO4S: 436.02; Found: 436.1.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous NH4Cl
  2. additiondiluted with CH2Cl2
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (silica gel, 5 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d4898d60128b41c68d2fa10b54cb95b6
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09376392B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes