1-Octyne → tert-Butyl-5-((4-(3-(6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-yl)prop-1-ynyl)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-(3-(4-Iodophenyl)prop-2-ynyl)-6-methoxy-1H-indol-3-yl)(3,4,5-trimethoxyphenyl)methanone	HCID 66726594	—
Product	tert-Butyl-5-((4-(3-(6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-yl)prop-1-ynyl)phenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate	HCID 131733940	48%

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 B was substituted for 5-iodo-2-tritylisoindoline in Example 2, Step D, the similar process afforded the title compound in 48% yield, as a light yellow paste. 1H-NMR (CDCl3) 1.43 (s, 3H); 1.46 (s, 9H); 1.49 (s, 3H); 3.84 (s, 6H); 3.9 (s, 3H); 3.91 (s, 3H); 4.00 (d, 2H, J=11.34 Hz); 4.1 (d, 2H, J=11.35 Hz); 5.08 (s, 2H); 5.19 (s, 1H); 6.95 (d, 1H, J=2.04 Hz); 7.00 (dd, 1H, J=2.18, 8.75 Hz); 7.11 (s, 2H); 7.3 (d, 2H, J=8.5 Hz); 7.35 (d, 2H, J=8.49 Hz); 7.74 (s, 1H); 8.25 (d, 1H, J=8.7 Hz).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09181182B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-a091e7d4b4664b95beb28217ede0bb63
Source note	uspto-grants-2015_11