Acetic Acid → HCID 117727770, compound

HRID 718564Notes

Reaction equation

HRID 718564 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) in DCM was cooled to 0° C. and treated with 10 μL of DMF followed by addition of oxalyl chloride (154 μL, 1.76 mmol). The resulting mixture was stirred at rt for 30 min and concentrated. The resultant residue was dried in vacuo for 15 min, dissolved in CH3CN (5 mL), and treated with a 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 organic layer was separated, dried over Na2SO4, and concentrated. The residue obtained was dried in vacuo 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. dry with materialThe resultant residue was dried in vacuo for 15 min
  3. dissolutiondissolved in CH3CN (5 mL)
  4. stirringThe resulting mixture was stirred for 1 h
  5. temperaturecooled to 0° C.
  6. stirringAfter stirring for 30 min
  7. washwashed with saturated NaHCO3 (2×25 mL)
  8. customThe organic layer was separated
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated
  11. customThe residue obtained
  12. customwas dried in vacuo for 15 min

Sources & evidence

ORD record
ord-70671875d21a4e2481b299fc75c5ba3e
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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