Trifluoroacetic acid → HCID 50908738, compound

HRID 1020687Notes

Reaction equation

HRID 1020687 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][N:19]([C:22]3[CH:23]=[CH:24][C:25]4[C:26]5[CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32][C:27]=5[N:28]([CH3:31])[C:29]=4[CH:30]=3)[C:18](=[O:43])[CH:17]=2)=[CH:12][CH:11]=1>C(Cl)Cl>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][N:19]([C:22]3[CH:23]=[CH:24][C:25]4[C:26]5[CH2:35][NH:34][CH2:33][CH2:32][C:27]=5[N:28]([CH3:31])[C:29]=4[CH:30]=3)[C:18](=[O:43])[CH:17]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57950370HCID 57950370, compound

Product 1

HCID 50908738HCID 50908738, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1.0 mL) was added to a solution of tert-butyl 7-(4-(4-methoxyphenyl)-2-oxopyridin-1(2H)-yl)-5-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (74 mg, 0.15 mmol) in CH2Cl2 (1 mL) under N2 and stirred for 2 h at ambient temperature. The mixture was concentrated, and the residue was partitioned between CH2Cl2 and saturated NaHCO3 solution. The organic phase was removed, and the aqueous phase was extracted with CH2Cl2 (4×25 mL). The combined organic extracts were washed with brine (25 mL), dried over Na2SO4 and concentrated under reduced pressure. Flash column chromatography (12 g ISCO CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 5 column volumes to 0:100 over 20 column volumes and hold for 5 column volumnes) yielded the title compound (46 mg, 78%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 7.60 (d, J=9.0 Hz, 2H), 7.50-7.46 (m, 2H), 7.36 (d, J=2.0 Hz, 1H), 7.05 (dd, J=8.5, 2.0 Hz, 1H), 7.00 (d, J=8.5 Hz, 2H), 6.86 (d, J=1.5 Hz, 1H), 6.49 (dd, J=7.0, 2.0 Hz, 1H), 4.08 (s, 2H), 3.87 (s, 3H), 3.63 (s, 3H), 3.27 (t, J=6.0 Hz, 2H), 2.77 (t, J=5.5 Hz, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between CH2Cl2 and saturated NaHCO3 solution
  3. customThe organic phase was removed
  4. extractionthe aqueous phase was extracted with CH2Cl2 (4×25 mL)
  5. washThe combined organic extracts were washed with brine (25 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c7a128767aa4c9b944338e64f8db14c
Source dataset
uspto-grants-2014_05
Patent number
US08716308B2

Reaction notes

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