Trifluoroacetic acid → 7-Bromo-9-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

HRID 930635Notes

Reaction equation

HRID 930635 reaction equation
C(OC([N:8]1[CH2:20][CH2:19][C:18]2[C:17]3[C:12](=[CH:13][C:14]([Br:21])=[CH:15][CH:16]=3)[N:11]([CH3:22])[C:10]=2[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Br:21][C:14]1[CH:13]=[C:12]2[C:17]([C:18]3[CH2:19][CH2:20][NH:8][CH2:9][C:10]=3[N:11]2[CH3:22])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57950468tert-butyl 7-bromo-9-methyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate

Product 1

HCID 579503917-Bromo-9-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indoleYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl-7-bromo-9-methyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (1.75 g, 4.79 mmol) was dissolved in CH2Cl2 (10 mL) and trifluoroacetic acid (TFA) (10 mL) was added. After stirring for 1 h, the mixture was diluted with methylene chloride (50 mL), washed with saturated Na2CO3 solution, dried over sodium sulfate and concentrated to provide the title compound (1.24 g, 97%) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 7.41 (d, J=1.4 Hz, 1H), 7.32 (d, J=8.3 Hz, 1H), 7.17 (dd, J=8.3, 1.4 Hz, 1H), 4.01 (s, 2H), 3.55 (s, 3H), 3.15 (t, J=6.0 Hz, 2H), 2.72 (t, J=5.7 Hz, 2H).

Workup

  1. washwashed with saturated Na2CO3 solution
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-bbd8fb144f654f5598a00ac8a3353460
Source dataset
uspto-grants-2016_03
Patent number
US09296743B2

Reaction notes

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