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【结 构 式】 
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【分子编号】49877 【品名】tributyl[5-(1,3-dioxolan-2-yl)-2-furyl]stannane 【CA登记号】 |
【 分 子 式 】C19H34O3Sn 【 分 子 量 】429.18716 【元素组成】C 53.17% H 7.98% O 11.18% Sn 27.66% |
合成路线1
该中间体在本合成路线中的序号：(VII)Williamson's ether synthesis between 2-chloro-4-nitrophenol (I) and 3-fluorobenzyl bromide (II) afforded ether (III). The nitro group of (III) was then reduced to the aniline (IV) by means of catalytic hydrogenation over Pt/C. Condensation of aniline (IV) with 4-chloro-6-iodoquinazoline (V) furnished the diaryl amine (VI). Subsequent Stille coupling between iodide (VI) and 5-dioxolanyl-2-(tributylstannyl)furan (VII) gave rise to adduct (VIII), which was further subjected to acid hydrolysis of the cyclic ketal to yield aldehyde (IX). Finally, reductive amination of (IX) with 2-(methanesulfonyl)ethylamine (X) in the presence of sodium triacetoxyborohydride provided the title compound.
| 【1】 Guntrip, S.B.; Lackey, K.E.; Cockerill, G.S.; Carter, M.C.; Smith, K.J. (Glaxo Group Ltd.); Bicyclic heteroaromatic cpds. as protein tyrosine kinase inhibitors. EP 1047694; WO 9935146 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 49872 | 1-Chloro-2-Hydroxy-5-Nitrobenzene; 2-Chloro-4-nitrophenol; 4-Nitro-2-chlorophenol; p-Nitro-o-chlorophenol | 619-08-9 | C6H4ClNO3 | 详情 | 详情 |
| (II) | 17221 | 3-Fluorobenzyl bromide; 1-(bromomethyl)-3-fluorobenzene | 456-41-7 | C7H6BrF | 详情 | 详情 |
| (III) | 49873 | 2-chloro-1-[(3-fluorobenzyl)oxy]-4-nitrobenzene; 2-chloro-4-nitrophenyl 3-fluorobenzyl ether | C13H9ClFNO3 | 详情 | 详情 | |
| (IV) | 49874 | 3-chloro-4-[(3-fluorobenzyl)oxy]phenylamine; 3-chloro-4-[(3-fluorobenzyl)oxy]aniline | C13H11ClFNO | 详情 | 详情 | |
| (V) | 49875 | 4-chloro-6-iodoquinazoline | 98556-31-1 | C8H4ClIN2 | 详情 | 详情 |
| (VI) | 49876 | N-[3-chloro-4-[(3-fluorobenzyl)oxy]phenyl]-N-(6-iodo-4-quinazolinyl)amine; N-[3-chloro-4-[(3-fluorobenzyl)oxy]phenyl]-6-iodo-4-quinazolinamine | C21H14ClFIN3O | 详情 | 详情 | |
| (VII) | 49877 | tributyl[5-(1,3-dioxolan-2-yl)-2-furyl]stannane | C19H34O3Sn | 详情 | 详情 | |
| (VIII) | 49878 | N-[3-chloro-4-[(3-fluorobenzyl)oxy]phenyl]-6-[5-(1,3-dioxolan-2-yl)-2-furyl]-4-quinazolinamine; N-[3-chloro-4-[(3-fluorobenzyl)oxy]phenyl]-N-[6-[5-(1,3-dioxolan-2-yl)-2-furyl]-4-quinazolinyl]amine | C28H21ClFN3O4 | 详情 | 详情 | |
| (IX) | 49879 | 5-(4-[3-chloro-4-[(3-fluorobenzyl)oxy]anilino]-6-quinazolinyl)-2-furaldehyde | C26H17ClFN3O3 | 详情 | 详情 | |
| (X) | 49880 | 2-(methylsulfonyl)-1-ethanamine; 2-(methylsulfonyl)ethylamine | C3H9NO2S | 详情 | 详情 |