6-Bromo-1-methylindole-2-carbaldehyde synthesis
- Product Name:6-Bromo-1-methylindole-2-carbaldehyde
- CAS Number:1382774-60-8
- Molecular formula:C10H8BrNO
- Molecular Weight:238.08
105191-12-6
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1382774-60-8
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Yield: 99%
Reaction Conditions:
Stage #1:6-bromo-1H-indole-2-carbaldehyde with sodium hydride in N,N-dimethyl-formamide;mineral oil at 0;Inert atmosphere;
Stage #2:methyl iodide in N,N-dimethyl-formamide;mineral oil at 0 - 20; for 4 h;
Steps:
16.c
Sodium hydride (60% weight dispersion in mineral oil, 80.0 mg, 1.98 mmol) was added to a solution of 6-bromo-1H-indole-2-carbaldehyde (371 mg, 1.66 mmol) in DMF (10.0 mL) at 0° C. under N2. Methyl iodide (0.124 mL, 1.98 mmol) was added, and the reaction mixture was allowed to warm slowly to room temperature. After stirring for 4 h, the mixture was quenched with H2O at 0° C., upon which a solid precipitated out of solution. The slurry was extracted with ethyl ether (3*). The combined organic layers was dried over Na2SO4, filtered and concentrated to give the title compound (422 mg, 99%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 9.89 (s, 1H), 7.59 (d, J=9.0 Hz, 2H), 7.28 (dd, J=8.5, 2.0 Hz, 1H), 7.22 (s, 1H), 4.07 (s, 3H).
References:
ALBANY MOLECULAR RESEARCH, INC. US2012/157469, 2012, A1 Location in patent:Page/Page column 29
16732-65-3
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1382774-60-8
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923197-75-5
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1382774-60-8
13 suppliers
$285.00/0.5 G