2,5-Dimethoxytetrahydrofuran → HCID 11347178, compound

HRID 916178Notes

Reaction equation

HRID 916178 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[C:17]([OH:19])=[O:18])=[CH:4][CH:3]=1.CO[CH:22]1[CH2:26][CH2:25][CH:24](OC)O1>C(O)(=O)C>[N:1]1([C:2]2[CH:3]=[CH:4][C:5]([N:8]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH:10]=[C:9]3[C:17]([OH:19])=[O:18])=[CH:6][CH:7]=2)[CH:22]=[CH:26][CH:25]=[CH:24]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 69435288HCID 69435288, compound

Product 1

HCID 11347178HCID 11347178, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-(4-aminophenyl)-1H-indole-2-carboxylic acid (0.4 g, 1.59 mmol) and 2,5-dimethoxytetrahydrofuran (0.50 g, 3.78 mmol) in 15 mL of glacial acetic acid was heated at 90° C. for 1.5 hours. After removing the solvent the residue was purified by by semi-preparative HPLC to afford the title compound (0.095 mg, 20%) as a beige solid: 1H NMR (DMSO-d6) δ 6.32 (s, 2H), 7.08 (d, J=8.4 Hz, 1H), 7.15-7.25 (m, 1H), 7.25-7.35 (m, 1H), 7.40-7.55 (m, 5H), 7.60-7.70 (m, 3H), 12.82 (br s, 1H); MS (ESI) m/z 303 (MH+); MS (ESI) m/z 301 ([M−H]−); HRMS calcd for C19H15N2O2: 303.1122; found (ESI+): 303.1124; Anal. calcd for C19H14N2O2.0.1H2O: C, 75.0; H, 4.71; N, 9.21. Found: C, 74.90; H, 4.42; N, 9.33.

Workup

  1. customAfter removing the solvent the residue
  2. customwas purified by by semi-preparative HPLC

Sources & evidence

ORD record
ord-44f25302761e46c588c4e2477ea66366
Source dataset
uspto-grants-2007_09
Patent number
US07268159B2

Reaction notes

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