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 → tert-Butyl-5-(4-(6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-ylsulfonyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710326Notes

Reaction equation

HRID 710326 reaction equation
[C:1]([O:5][C:6](=[O:52])[NH:7][C:8]1([C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([N:27]3[C:35]4[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=4)[C:29]([C:38](=[O:51])[C:39]4[CH:44]=[C:43]([O:45][CH3:46])[C:42]([O:47][CH3:48])=[C:41]([O:49][CH3:50])[CH:40]=4)=[CH:28]3)(=[O:26])=[O:25])=[CH:20][CH:19]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([O:5][C:6](=[O:52])[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([N:27]3[C:35]4[C:30](=[CH:31][CH:32]=[C:33]([O:36][CH3:37])[CH:34]=4)[C:29]([C:38](=[O:51])[C:39]4[CH:44]=[C:43]([O:45][CH3:46])[C:42]([O:47][CH3:48])=[C:41]([O:49][CH3:50])[CH:40]=4)=[CH:28]3)(=[O:26])=[O:25])=[CH:20][CH:19]=2)[CH2:13][O:12][C:11]([CH3:14])([CH3:15])[O:10][CH2:9]1)([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 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-ylcarbamate

Product 1

HCID 131733939tert-Butyl-5-(4-(6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-ylsulfonyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of the product of Step D (0.09 g, 0.12 mmol) and 10% Pd/C (0.04 g) was stirred for 16 h under H2 (balloon). The catalyst was removed by filtration through Celite pad, the filtrate evaporated to dryness, to give the product (0.065 g; 73%), as pale paste. 1H-NMR (CDCl3) 1.37 (s, 3H); 1.40 (s, 3H); 1.42 (s, 9H); 1.87-1.93 (m, 2H); 2.52-2.57 (m, 2H); 3.62 (d, 2H, J=11.77 Hz); 3.80 (d, 2H, J=11.55 Hz); 3.89 (s, 3H); 3.90 (s, 6H); 3.95 (s, 3H); 6.98 (dd, 1H, J=2.26, 8.80 Hz); 7.11 (s, 2H); 7.26 (d, 2H, J=8.37 Hz); 7.49 (d, 1H, J=2.16 Hz); 7.78 (d, 2H, J=8.37 Hz); 7.91 (s, 1H); 8.09 (d, 1H, J=8.8 Hz).

Workup

  1. customThe catalyst was removed by filtration through Celite pad
  2. customthe filtrate evaporated to dryness
  3. customto give the product (0.065 g; 73%)

Sources & evidence

ORD record
ord-6f0c4ab32bf8404fb2ef6097f4834a04
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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