Dichloromethane → 5-(1H-indol-2-yl)-2,4-dimethoxybenzaldehyde

HRID 347350Notes

Reaction equation

HRID 347350 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[CH:22]=[C:21]([CH:23]=[O:24])[C:20]([O:25][CH3:26])=[CH:19][C:18]=1[O:27][CH3:28])=O)(C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].C(Cl)Cl>C1COCC1>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[C:18]([O:27][CH3:28])=[CH:19][C:20]([O:25][CH3:26])=[C:21]([CH:22]=1)[CH:23]=[O:24]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2724141Tetrabutylammonium Fluoride2×HCID 161163072-(5-Formyl-2,4-dimethoxyphenyl)indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 161156215-(1H-indol-2-yl)-2,4-dimethoxybenzaldehydeYield 30.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ex-32B: 2-(5-Formyl-2,4-dimethoxyphenyl)indole-1-carboxylic acid tert-butyl ester (Ex-32A, 2.0 g, 5.2 mmol) was dissolved in 100 ml of THF, and Bu4NF (6.86 g, 26 mmol) was added. The reaction mixture was stirred at room temperature overnight. No significant reaction occurred under these conditions by HPLC. Then, additional Bu4NF (6.86 g, 26 mmol) was added to the mixture, and the mixture was stirred at reflux for 4 days. The reaction reached about 50% completion (HPLC). The reaction mixture was poured into CH2Cl2, and washed with water and brine. The organic phase was dried over MgSO4, and concentrated. The residue was purified by column chromatography (EtOAc/hexanes, 2:1) to give 0.45 g (30%) of 5-(1H-indol-2-yl)-2,4-dimethoxybenzaldehyde. 1H-NMR (300 MHz, CDCl3) δ 10.37 (s, 1H), 9.25 (br, 1H), 8.28 (s, 1H), 7.63(d, J=8 Hz, 1H), 7.39 (d, J=8 Hz, 1H), 7.08–7.20 (m, 2H), 6.92(d, J=2 Hz, 1H), 6.56 (s, 1H) 4.11(s, 3H), 4.00 (s, 3H). HMRS (EI) calcd. for C17H15NO3: 281.1052 (M+); Found: 281.1049.

Workup

  1. customNo significant reaction
  2. stirringthe mixture was stirred
  3. temperatureat reflux for 4 days
  4. washwashed with water and brine
  5. dry with materialThe organic phase was dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (EtOAc/hexanes, 2:1)

Sources & evidence

ORD record
ord-a787577a0cea41999143fdbbb899cfcf
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Reaction notes

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