1-Octyne → Tert-butyl-5-((4-(6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1h-indol-1-ylsulfonyl)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710325Notes

Reaction equation

HRID 710325 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:16]#[CH:17])[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C#CCCCCCC.Br[C:28]1[CH:33]=[CH:32][C:31]([S:34]([N:37]2[C:45]3[C:40](=[CH:41][CH:42]=[C:43]([O:46][CH3:47])[CH:44]=3)[C:39]([C:48]([C:50]3[CH:55]=[C:54]([O:56][CH3:57])[C:53]([O:58][CH3:59])=[C:52]([O:60][CH3:61])[CH:51]=3)=[O:49])=[CH:38]2)(=[O:36])=[O:35])=[CH:30][CH:29]=1.IC1C=C2C(=CC=1)CN(C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C2>>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:16]#[C:17][C:28]2[CH:33]=[CH:32][C:31]([S:34]([N:37]3[C:45]4[C:40](=[CH:41][CH:42]=[C:43]([O:46][CH3:47])[CH:44]=4)[C:39]([C:48](=[O:49])[C:50]4[CH:51]=[C:52]([O:60][CH3:61])[C:53]([O:58][CH3:59])=[C:54]([O:56][CH3:57])[CH:55]=4)=[CH:38]3)(=[O:35])=[O:36])=[CH:30][CH:29]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 123701-OctyneHCID 115143851,1-Dimethylethyl N-(5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamateHCID 667262485-Iodo-2-tritylisoindolineHCID 66726837(1-(4-Bromophenylsulfonyl)-6-methoxy-1h-indol-3-yl)(3,4,5-trimethoxyphenyl)methanone

Product 1

HCID 131733938Tert-butyl-5-((4-(6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1h-indol-1-ylsulfonyl)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamateYield 56%

Procedure

When tert-butyl-5-ethynyl-2,2-dimethyl-1,3-dioxan-5-ylcarbamate was substituted for 1-octyne and the product of Step C was substituted for 5-iodo-2-tritylisoindoline in Example 2, Step D, the similar process afforded the title compound in 56% yield, as yellow paste. 1H-NMR (CDCl3) 1.41 (s, 3H); 1.43 (s, 9H); 1.45 (s, 3H); 3.88 (s, 3H), 3.90 (s, 6H), 3.95 (s, 3H); 3.96 (d, 2H, J=11.58 Hz); 4.05 (d, 2H, J=11.45 Hz); 7.0 (dd, 1H, J=2.25, 8.82 Hz); 7.00 (s, 2H); 7.44 (broad s, 1H); 7.46 (d, 2H, J=8.7 Hz); 7.80 (d, 2H, J=8.61 Hz); 7.89 (s, 1H); 8.08 (d, 1H, J=8.82 Hz),

Sources & evidence

ORD record
ord-5a7ce4d01d564615ab71313bb6fc9192
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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