Dimethyl Sulfoxide → HCID 58368654, compound

HRID 1192570Notes

Reaction equation

CS(C)=O.C(Cl)(=O)C(Cl)=O.[Br:11][C:12]1[CH:21]=[C:20]([CH2:22][OH:23])[C:19]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[N:17]2.C(N(CC)CC)C>C(Cl)Cl>[Br:11][C:12]1[CH:21]=[C:20]([CH:22]=[O:23])[C:19]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=2)=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[N:17]2

Participants

Conditions

Temperature: -78 °C

Procedure

Dimethyl sulfoxide (0.038 mL, 0.54 mmol) was added to oxalyl chloride (0.0286 mL, 0.339 mmol) in methylene chloride (1.26 mL) at −78° C. After 10 minutes, [5-bromo-8-(3-fluorophenyl)quinolin-7-yl]methanol (0.075 g, 0.22 mmol) in methylene chloride (2.53 mL) was added and the resulting mixture was stirred at −78° C. for 30 minutes. Triethylamine (0.157 mL, 1.13 mmol) was then added and the mixture was stirred for 5 hours to room temperature. After quenching with water, the mixture was extracted with methylene chloride. The organic layers were combined, washed with brine, dried over magnesium sulfate and evaporated to dryness. The resulting mixture was purified on silica gel, eluting with 0 to 50% ethyl acetate in hexane, to give the desired product (49 mg, 66%). LCMS calculated for C16H10BrFNO (M+H)+: m/z=330.0; Found: 330.0.

Workup

stirringthe mixture was stirred for 5 hours to room temperature
customAfter quenching with water
extractionthe mixture was extracted with methylene chloride
washwashed with brine
dry with materialdried over magnesium sulfate
customevaporated to dryness
customThe resulting mixture was purified on silica gel
washeluting with 0 to 50% ethyl acetate in hexane

Sources & evidence

ORD record: ord-ee4d190058cb4e5b9b3ca1232736918b
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

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