ChemicalBook CAS DataBase List 4-Bromo-7-azaindole

4-Bromo-7-azaindole synthesis

4synthesis methods

Product Name:4-Bromo-7-azaindole
CAS Number:348640-06-2
Molecular formula:C7H5BrN2
Molecular Weight:197.03

55052-24-9
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$80.00/5 g

348640-06-2
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$6.00/250mg

Yield:348640-06-2 56%

Reaction Conditions:

with tetramethylammonium bromide;Methanesulfonic anhydride in N,N-dimethyl-formamide at 0 - 20; for 5 h;

Steps:

1H-pyrrolo[2,3-b]pridine 7-oxide 21 (3.0 g, 22.4 mmol) and tetramethylammonium (4.13 g, 1.2 eq) were dissolved in DMF (30 ml). The Ms₂O (7.8 g, 2.0 eq) was added at 0 in small portions. The obtained mixture was stirred for 1 h at 0 and for 4 h at room temperature and diluted with water (60 ml). The PH was adjusted to 7 with solid NaOH, and more than 130 ml of water was added. The resulting suspension was kept at 5 for 1 h. The precipitate was separated by filtration, washed with ice-water (2 * 20 ml), and dried over P₂O₅ in vacuum ovento give 4-bromo-1H-pyrrolo[2,3-b]pyridine (2.47 g, 56%). MS (ESI) m/z 196.9 [M+H]⁺. ¹H NMR (400 Hz, CDCl₃) δ 10.77 (br, s, 1H), 8.14 (d, J = 5.2 Hz1H), 7.42 (s, 1H), 7.31 (d, J = 5.1 Hz1H), 6.57 (s, 1H).

References:

Chang, Shaohua;Zhang, Zhang;Zhuang, Xiaoxi;Luo, Jinfeng;Cao, Xianwen;Li, Honglin;Tu, Zhengchao;Lu, Xiaoyun;Ren, Xiaomei;Ding, Ke [Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,# 2,p. 1208 - 1212] Location in patent:supporting information; experimental part

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55052-24-9
151 suppliers
$80.00/5 g

7143-01-3 Synthesis