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

Participants

Role	Name	HCID	Charge
Reactant	1-Octyne	HCID 12370	—
Reactant	1,1-Dimethylethyl N-(5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamate	HCID 11514385	—
Reactant	5-Iodo-2-tritylisoindoline	HCID 66726248	—
Reactant	(1-(4-Bromophenylsulfonyl)-6-methoxy-1h-indol-3-yl)(3,4,5-trimethoxyphenyl)methanone	HCID 66726837	—
Product	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	HCID 131733938	56%

Reaction Steps

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),

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181182B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-5a7ce4d01d564615ab71313bb6fc9192
Source note	uspto-grants-2015_11