Trifluoroacetic acid → HCID 59418746, compound

HRID 2178259Notes

Reaction equation

HRID 2178259 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]([C:12]1[N:17]=[C:16]([C:18]2[CH:27]=[C:26]3[C:21]([CH2:22][CH2:23][CH2:24][N:25]3C(OC(C)(C)C)=O)=[CH:20][CH:19]=2)[CH:15]=[CH:14][C:13]=1[O:35][S:36]([C:39]([F:42])([F:41])[F:40])(=[O:38])=[O:37])=[O:11]>C(Cl)Cl>[NH:25]1[C:26]2[C:21](=[CH:20][CH:19]=[C:18]([C:16]3[N:17]=[C:12]([C:10]([O:9][CH3:8])=[O:11])[C:13]([O:35][S:36]([C:39]([F:41])([F:42])[F:40])(=[O:38])=[O:37])=[CH:14][CH:15]=3)[CH:27]=2)[CH2:22][CH2:23][CH2:24]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59418739HCID 59418739, compound

Product 1

HCID 59418746HCID 59418746, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (18 mL) was added to tert-butyl 7-(6-(methoxycarbonyl)-5-(trifluoromethylsulfonyloxy)pyridin-2-yl)-3,4-dihydroquinoline-1(2H)-carboxylate (29E) (2.00 g, 3.9 mmol) in anhydrous DCM (25 mL). The reaction mixture was stirred at rt for 1.5 hours, concentrated under reduced pressure, diluted with DCM, and washed with saturated NaHCO3. The aqueous phase was extracted with DCM. The combined organic phases were dried over MgSO4, filtered, and concentrated under reduced pressure to provide the desired product methyl 6-(1,2,3,4-tetrahydroquinolin-7-yl)-3-(trifluoromethylsulfonyloxy)picolinate (29F) in sufficient purity for subsequent use. 1H NMR (300 MHz, CDCl3) δ 7.88 (1H d), 7.66 (1H, d), 7.39 (1H, d) 7.29 (1H, dd), 7.08 (1H, d), 4.03 (3H, s), 3.39 (2H, m), 2.83 (2H, t), 2.02 (2H, m).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with DCM
  3. washwashed with saturated NaHCO3
  4. extractionThe aqueous phase was extracted with DCM
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-875814a86c0745e28ceb24714c23457c
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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