1-Octyne → tert-Butyl 5-((4-((6-methoxybenzofuran-2-yl)ethynyl)phenyl)-ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710334노트

반응식

HRID 710334 반응식
[C:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:6]=2[CH:7]=1)#[CH:2].C#CCCCCCC.[C:22]([O:26][C:27](=[O:46])[NH:28][C:29]1([C:37]#[C:38][C:39]2[CH:44]=[CH:43][C:42](I)=[CH:41][CH:40]=2)[CH2:34][O:33][C:32]([CH3:36])([CH3:35])[O:31][CH2:30]1)([CH3:25])([CH3:24])[CH3:23].IC1C=C2C(=CC=1)CN(C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C2>>[CH3:13][O:12][C:10]1[CH:9]=[CH:8][C:6]2[CH:7]=[C:3]([C:1]#[C:2][C:42]3[CH:43]=[CH:44][C:39]([C:38]#[C:37][C:29]4([NH:28][C:27](=[O:46])[O:26][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:34][O:33][C:32]([CH3:36])([CH3:35])[O:31][CH2:30]4)=[CH:40][CH:41]=3)[O:4][C:5]=2[CH:11]=1

참가 물질

5

반응물 4

HCID 123701-OctyneHCID 667262485-Iodo-2-tritylisoindolineHCID 66726604tert-Butyl 5-((4-iodophenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateHCID 717417602-Ethynyl-6-methoxybenzofuran

생성물 1

HCID 86661775tert-Butyl 5-((4-((6-methoxybenzofuran-2-yl)ethynyl)phenyl)-ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate수율 90%

실험 절차

When the product of Step D was substituted for 1-octyne and tert-butyl-5-((4-iodophenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate was substituted for 5-iodo-2-tritylisoindoline in Example 2, Step D, the similar process afforded the title compound in 90% yield, as a light yellow paste. 1H-NMR (CDCl3) 1.44 (s, 3H); 1.47 (s, 9H); 1.49 (s, 3H); 3.85 (s, 3H); 4.02 (d, 2H, J=11.34 Hz); 4.09 (d, 2H, J=11.38 Hz); 5.20 (s, 1H); 6.88 (dd, 1H, J=2.24, 8.6 Hz); 6.93 (s, 1H); 6.96 (d, 1H, J=1.97 Hz); 7.38-7.41 (m, 3H); 7.46 (d, 2H, J=8.44 Hz).

출처 및 근거

ORD 기록
ord-b48a6cb5a1e340a89f3b9bc7351c31de
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181182B2

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