Trifluoroacetic acid → HCID 59418746, compound

HRID 1641095Notes

Reaction equation

HRID 1641095 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-8cf5a069ed9d4504b6740a412c6552e9
Source dataset
uspto-grants-2012_02
Patent number
US08114893B2

Reaction notes

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