2,5-Dimethoxytetrahydrofuran → ethyl 1-benzyl-3-phenyl-5-(1H-pyrrol-1-yl)-1H-indole-2-carboxylate

HRID 915339Notes

Reaction equation

HRID 915339 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:5]2[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CO[CH:31]1[CH2:35][CH2:34][CH:33](OC)O1>C(O)(=O)C>[CH2:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([N:1]3[CH:31]=[CH:35][CH:34]=[CH:33]3)=[CH:10][CH:9]=2)[C:5]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[C:6]1[C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 69229300ethyl 5-amino-1-benzyl-3-phenyl-1H-indole-2-carboxylate

Product 1

HCID 69341286ethyl 1-benzyl-3-phenyl-5-(1H-pyrrol-1-yl)-1H-indole-2-carboxylateYield 95.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of ethyl 5-amino-1-benzyl-3-phenyl-1H-indole-2-carboxylate (0.74 g, 2 mmol), 2,5-dimethoxytetrahydrofuran (0.40 g, 3 mmol) in acetic acid was heated to 90° C. for 3 h. The reaction was cooled and concentrated. The residue was then purified by flash silica gel chromatography (hexanes/ethyl acetate 5/1) to afforded 0.8 g (95%) of ethyl 1-benzyl-3-phenyl-5-(1H-pyrrol-1-yl)-1H-indole-2-carboxylate as an off-white solid: 1H NMR (CDCl3) δ 0.97 (t, J=7.1 Hz, 3 H), 4.11 (q, J=7.1 Hz, 2 H), 5.84 (s, 2 H), 6.30 (t, J=2.1 Hz, 2 H), 7.01 (t, J=2.1 Hz, 2 H), 7.10-7.50 (m, 13 H); MS (ESI) m/z 421 (MH+); HRMS calcd for C28H25N2O2: 421.1917; found (ESI+): 421.1903; Anal. calcd for C28H24N2O2: C, 79.98; H, 5.75; N, 6.66. Found: C, 80.03; H, 5.67; N, 6.49.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated
  3. customThe residue was then purified by flash silica gel chromatography (hexanes/ethyl acetate 5/1)

Sources & evidence

ORD record
ord-74956ddafa9743bab4170c6e54ed516c
Source dataset
uspto-grants-2007_09
Patent number
US07265148B2

Reaction notes

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