Trifluoroacetic acid → HCID 68462228, compound

HRID 501196Notes

Reaction equation

HRID 501196 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([C:15]4[N:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][N:16]=4)[CH2:14][C:5]=3[C:4]=2[CH:3]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][CH:6]3[CH2:11][CH2:12][N:13]([C:15]4[N:16]=[CH:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][N:20]=4)[CH2:14][CH:5]3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68464048HCID 68464048, compound

Product 1

HCID 68462228HCID 68462228, compoundYield 27.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 2-(8-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)pyrimidine-5-carboxylate was obtained from Example 7 and 8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole using the method described in Example 12. To a stirred solution of methyl 2-(8-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)pyrimidine-5-carboxylate (0.250 g, 0.776 mmol) in dry DCM, TFA (2.5 ml, 129.81 mmol) was added and stirred for 30 min. Then triethylsilane (2.5 ml, 62.6 mmol) was added at room temperature and stirred for 2 h. The progress of the reaction was monitored by TLC and after completion, the reaction mixture was diluted with DCM and washed with saturated solution of sodium bicarbonate and the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to furnish methyl 2-(8-methyl-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indol-2-yl)pyrimidine-5-carboxylate (69 mg, 27.5%). 1H NMR (200 MHz, CDCl3): δ 1.69 (m, 2H), 2.35 (s, 3H), 2.7 (m; 2H), 3.01 (m, 4H), 3.90 (s, 3H), 6.23 (m, 1H), 6.80 (2H, m), 8.91 (s, 2H); m/e=325 (M+1).

Workup

  1. stirringstirred for 2 h
  2. washwashed with saturated solution of sodium bicarbonate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dfb3d80175134165b2a1cf5832074905
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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