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Trifluoroacetic acid → 2-(1-ethyl-4-methoxy-6-phenyl-1H-indol-3-yl)-N,N-dimethylethanamine

HRID 1404147
Notes
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Reaction equation

HRID 1404147 reaction equation
[CH3:1][N:2]([CH3:25])[CH2:3][CH:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][C:13]=2[O:15][CH3:16])[N:8]([CH2:23][CH3:24])[CH:7]=1)O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:23]([N:8]1[C:9]2[C:14](=[C:13]([O:15][CH3:16])[CH:12]=[C:11]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:10]=2)[C:6]([CH2:4][CH2:3][N:2]([CH3:25])[CH3:1])=[CH:7]1)[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 583040302-(dimethylamino)-1-(1-ethyl-4-methoxy-6-phenyl-1H-indol-3-yl)ethanol

Product 1

HCID 509956292-(1-ethyl-4-methoxy-6-phenyl-1H-indol-3-yl)-N,N-dimethylethanamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

36-5 (68 mg, 0.2 mmol) was dissolved in DCM (2 mL) and triethylsilane (0.32 mL, 2.0 mmol) was added at 0° C. Trifluoroacetic acid (126 uL, 1.6 mmol) was added dropwise. After 20 minutes, the reaction mixture was quenched with saturated aqueous sodium bicarbonate and then diluted with DCM. The organic layer was dried over MgSO4, filtered, and evaporated. The resulting residue was purified on silica gel column chromatography eluting with DCM/methanol (0-10%) containing 0.1% NH4OH to give the desired product. The product was acidified with HCl to afford 36-6 (19.6 mg, 27%) as an off-white solid. 1H NMR (300 MHz, D2O): δ (ppm) 7.62 (m, 2H), 7.42-7.24 (m, 4H), 7.06 (s, 1H), 6.78 (s, 1H), 4.04 (q, J=7.5 Hz, 2H), 3.88 (s, 3H), 3.31 (t, J=8.4 Hz, 2H), 3.12 (t, J=7.5 Hz, 2H), 2.76 (s, 6H), 1.24 (s, 7.5 Hz, 3H). LCMS: calc 322.4 and found: 323.1 [MH]+.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous sodium bicarbonate
  2. additiondiluted with DCM
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting residue was purified on silica gel column chromatography
  7. washeluting with DCM/methanol (0-10%)
  8. additioncontaining 0.1% NH4OH

Sources & evidence

ORD record
ord-d7bacca5d91e467e94a786789d7182f1
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08912220B2

Reaction notes

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