tert-Butyl-2,2-dimethyl-5-((4-(3-(3-(2,2,2-trifluoroacetyl)-1H-indol-1-yl)prop-1-ynyl)phenyl)ethynyl)-1,3-dioxan-5-ylcarbamate → tert-Butyl-2,2-dimethyl-5-(4-(3-(3-(2,2,2-trifluoroacetyl)-1H-indol-1-yl)propyl)phenethyl)-1,3-dioxan-5-ylcarbamate

HRID 710315Notes

Reaction equation

HRID 710315 reaction equation
[C:1]([O:5][C:6](=[O:42])[NH:7][C:8]1([C:16]#[C:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]#[C:25][CH2:26][N:27]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29]([C:36](=[O:41])[C:37]([F:40])([F:39])[F:38])=[CH:28]3)=[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:42])[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH2:26][N:27]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29]([C:36](=[O:41])[C:37]([F:40])([F:38])[F:39])=[CH:28]3)=[CH:22][CH:23]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 131733934tert-Butyl-2,2-dimethyl-5-((4-(3-(3-(2,2,2-trifluoroacetyl)-1H-indol-1-yl)prop-1-ynyl)phenyl)ethynyl)-1,3-dioxan-5-ylcarbamate

Product 1

HCID 131733935tert-Butyl-2,2-dimethyl-5-(4-(3-(3-(2,2,2-trifluoroacetyl)-1H-indol-1-yl)propyl)phenethyl)-1,3-dioxan-5-ylcarbamate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of the product of Step D (0.6 g, 0.1 mmol) and 10% Pd/C (0.03 g) was stirred for 16 h under H2 (balloon). The catalyst was removed by filtration through Celite pad and filtrate evaporated to give the product (0.019 g; 32%), as pale paste. 1H-NMR (CDCl3) 1.4 (s, 3H); 1.42 (s, 3H); 1.46 (s, 9H); 1.94-2.0 (m, 2H); 2.22-2.29 (m, 2H); 2.51-2.57 (m, 2H); 2.63 (tr, 2H, J=7.30 Hz); 3.67 (d, 2H, J=11.79 Hz); 3.88 (d, 2H, J=11.69 Hz); 4.17 (tr, 2H, J=7.14 Hz); 4.98 (s, 1H); 7.05 (d, 2H, J=8.06 Hz); 7.11 (d, 2H, J=8.06 Hz); 7.30-7.38 (m, 3H); 7.85 (b, 1H); 8.37-8.42 (m, 1H).

Workup

  1. customThe catalyst was removed by filtration through Celite pad and filtrate
  2. customevaporated
  3. customto give the product (0.019 g; 32%)

Sources & evidence

ORD record
ord-5181b84f20244d01a3308a9e5813d162
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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