Technology Process of 5-Methoxy-1-methyl-2-(3-methyl-2-pyridyl)-1H-indole-3-carbaldehyde
There total 7 articles about 5-Methoxy-1-methyl-2-(3-methyl-2-pyridyl)-1H-indole-3-carbaldehyde which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
5-Methoxy-2-(3-methyl-2-pyridyl)-1H-indole-3-carbaldehyde;
With
potassium hexamethylsilazane;
In
tetrahydrofuran; toluene;
at -78 ℃;
for 0.5h;
methyl iodide;
In
tetrahydrofuran; toluene;
at -78 - 20 ℃;
for 1h;
Further stages.;
DOI:10.1039/b001685n
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 100 percent / DMAP / tetrahydrofuran / 16 h / 20 °C
2.1: lithium tetramethylpiperidie / tetrahydrofuran / 1.33 h / -78 °C
2.2: tetrahydrofuran / 0.5 h / -78 °C
3.1: aq. HCl / tetrahydrofuran / 20 °C
4.1: 77 percent / aq. Na2CO3 / Pd(PPh3)4 / 1,2-dimethoxy-ethane / 18 h / Heating
5.1: 86 percent / SiO2 / 0.05 h / Microwave irradiation (700 W)
6.1: 84 percent / POCl3 / 1 h / 35 °C
7.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C
7.2: 83 percent / tetrahydrofuran; toluene / 1 h / -78 - 20 °C
With
hydrogenchloride; dmap; 2,2,6,6-tetramethylpiperidinyl-lithium; silica gel; potassium hexamethylsilazane; sodium carbonate; trichlorophosphate;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,2-dimethoxyethane; toluene;
1.1: Acylation / 2.1: Metallation / 2.2: Substitution / 3.1: Hydrolysis / 4.1: Arylation / 5.1: Boc cleavage / 6.1: Formylation / 7.1: Metallation / 7.2: Methylation;
DOI:10.1039/b001685n
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: lithium tetramethylpiperidie / tetrahydrofuran / 1.33 h / -78 °C
1.2: tetrahydrofuran / 0.5 h / -78 °C
2.1: aq. HCl / tetrahydrofuran / 20 °C
3.1: 77 percent / aq. Na2CO3 / Pd(PPh3)4 / 1,2-dimethoxy-ethane / 18 h / Heating
4.1: 86 percent / SiO2 / 0.05 h / Microwave irradiation (700 W)
5.1: 84 percent / POCl3 / 1 h / 35 °C
6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C
6.2: 83 percent / tetrahydrofuran; toluene / 1 h / -78 - 20 °C
With
hydrogenchloride; 2,2,6,6-tetramethylpiperidinyl-lithium; silica gel; potassium hexamethylsilazane; sodium carbonate; trichlorophosphate;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,2-dimethoxyethane; toluene;
1.1: Metallation / 1.2: Substitution / 2.1: Hydrolysis / 3.1: Arylation / 4.1: Boc cleavage / 5.1: Formylation / 6.1: Metallation / 6.2: Methylation;
DOI:10.1039/b001685n
