Triethylamine → HCID 57791874, compound

HRID 1186290Notes

Reaction equation

HRID 1186290 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH:18]=1)([O-:3])=[O:2].[O:19]1CCO[CH2:21][CH2:20]1.C(N(CC)CC)C.BrCCO>C(Cl)Cl.[OH-].[Na+]>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13]1[CH2:14][CH2:15][N:16]([CH2:21][CH2:20][OH:19])[CH2:17][CH:18]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 108982-BromoethanolHCID 312751,4-DioxaneHCID 532635-nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 57791874HCID 57791874, compoundYield 36.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 5-nitro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (0.55 g, 2.261 mmol) in dry CH2Cl2:1,4-dioxane (15 mL, 2:1) was treated with triethylamine (0.636 mL, 4.52 mmol), followed by 2-bromoethanol (0.176 mL, 2.487 mmol) at room temperature. Only starting material was observed after stirring for 4 h at room temperature. The reaction was then refluxed for 24 h. The reaction was brought to room temperature, diluted with 1 N NaOH solution (25 mL) and product was extracted into CH2Cl2 (2×25 mL). The combined CH2Cl2 layer was washed with brine (20 mL) and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95) to obtain 2-(4-(5-nitro-1H-indol-3-yl)-5,6-dihydropyridin-1(2H)-yl)ethanol (0.24 g, 36.9%) as a dark yellow solid. 1H NMR (DMSO-d6) δ 11.86 (s, 1H), 8.68 (d, 1H, J=2.1 Hz), 8.01 (dd, 1H, J=2.4, 9.0 Hz), 7.65 (s, 1H), 7.55 (d, 1H, J=9.0 Hz), 6.16 (s, 1H), 4.42 (t, 1H, J=5.4 Hz), 3.56 (q, 2H), 3.18 (t, 2H, J=6.3 Hz), 2.69 (t, 2H, J=5.4 Hz), 2.54-2.50 (m, 4H); ESI-MS (m/z, %): 288 (MH+, 100).

Workup

  1. temperatureThe reaction was then refluxed for 24 h
  2. customwas brought to room temperature
  3. extractionwas extracted into CH2Cl2 (2×25 mL)
  4. washThe combined CH2Cl2 layer was washed with brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. customSolvent was evaporated
  7. customcrude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-f68100ea17e24527abc25547a0e4aaed
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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