ChemicalBook CAS DataBase List 3-(2-chloropyriMidin-4-yl)-1-Methylindole

3-(2-chloropyriMidin-4-yl)-1-Methylindole synthesis

7synthesis methods

Product Name:3-(2-chloropyriMidin-4-yl)-1-Methylindole
CAS Number:1032452-86-0
Molecular formula:C13H10ClN3
Molecular Weight:243.69

945016-63-7 Synthesis

945016-63-7
80 suppliers
$44.00/100mg

74-88-4
340 suppliers
$15.00/10g

3-(2-chloropyriMidin-4-yl)-1-Methylindole

1032452-86-0
287 suppliers
$9.00/1g

Yield:1032452-86-0 96%

Reaction Conditions:

Stage #1: 3-(2-chloro-pyrimidin-4-yl)-1H-indolewith sodium hydride in tetrahydrofuran;mineral oil at 0; for 0.5 h;
Stage #2: methyl iodide in tetrahydrofuran;mineral oil at 0; for 3 h;

Steps:

130 Intermediate 130: 3-(2-Chloropyrimidin-4-yl)-1-methylindole

NaH (1.707 g, 42.68 mmol, 40% dispersion in mineral oil) was added in small portions to a cooled (0°C) mixture of 3-(2-chloropyrimidin-4-yl)-1H-indole (Intermediate 131, 8.168 g, 35.57 mmol) in THF (250 mL). The resulting mixture was stirred at 0°C for 0.5h and then CH₃I (2.67 mL, 42.68 mmol) was added and the mixture stirred at 0°C for a further 3h. The reaction was quenched by the addition of sat. NaHCO₃ (25 mL). The mixture was then diluted with EtOAc (100 mL), and the resulting solution was washed with sat. NaHCO₃ (50 mL), water (50 mL) and sat. brine (50 mL). The organic solution was then concentrated in vacuo. Purification by FCC, eluting with 0-20% CH₃OH in CH₂Cl₂ gave the title compound (8.35 g, 96%) as a pale yellow solid; ¹H NMR: 3.90 (3H, s), 7.30 (2H, pd), 7.54-7.60 (1H, m), 7.82 (1H, d), 8.38-8.44 (1H, m), 8.49 (1H, s), 8.53 (1H, d); m/z: ES⁺ MH⁺ 244.

References:

WO2013/14448,2013,A1 Location in patent:Page/Page column 138

3934-20-1 Synthesis