Acetic Acid → HCID 117727770, compound

HRID 1772680Notes

Reaction equation

HRID 1772680 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]1[CH2:14][CH:13]([C:15]([OH:17])=O)[CH2:12]1.[C:18](Cl)(=O)C(Cl)=O.[Si](C=[N+]=[N-])(C)(C)C.[BrH:31].C(O)(=O)C>C(Cl)Cl.CN(C=O)C>[Br:31][CH2:18][C:15]([CH:13]1[CH2:12][CH:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH2:14]1)=[O:17]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 65578Oxalyl chlorideHCID 167693TrimethylsilyldiazomethaneHCID 117728320HCID 117728320, compound

Product 1

HCID 117727770HCID 117727770, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-(quinolin-2-yl)cyclobutanecarboxylic acid (200 mg, 0.800 mmol, as prepared above) in DCM was cooled to 0° C. and treated with 10 μL of DMF followed by oxalyl chloride (154 μL, 1.76 mmol). The resulting mixture was stirred at rt for 30 min and concentrated. The residue obtained was dried under reduced pressure for 15 min before being dissolved in CH3CN (5 mL) and treated with 2 M solution of TMSCHN2 in hexanes (0.88 mL, 1.76 mmol). The resulting mixture was stirred for 1 h, cooled to 0° C. and treated with 33 wt % HBr in acetic acid (0.35 mL, 1.76 mmol) dropwise. After stirring for 30 min, the reaction mixture was diluted with DCM (25 mL) and washed with saturated NaHCO3 (2×25 mL). The DCM layer was separated, dried over Na2SO4, filtered, and concentrated. The residue obtained was dried under reduced pressure for 15 min to obtain 2-bromo-1-(3-(quinolin-2-yl)cyclobutyl)ethanone as a viscous oil which was used without further purification in the next step.

Workup

  1. concentrationconcentrated
  2. customThe residue obtained
  3. customwas dried under reduced pressure for 15 min
  4. dissolutionbefore being dissolved in CH3CN (5 mL)
  5. stirringThe resulting mixture was stirred for 1 h
  6. temperaturecooled to 0° C.
  7. stirringAfter stirring for 30 min
  8. washwashed with saturated NaHCO3 (2×25 mL)
  9. customThe DCM layer was separated
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe residue obtained
  14. customwas dried under reduced pressure for 15 min

Sources & evidence

ORD record
ord-ec23800f9aef40189a0d6d07484f03a3
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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