tert-Butyl 5-((4-((6-methoxybenzofuran-2-yl)ethynyl)phenyl)-ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate → Tert-butyl-5-(4-(2-(6-methoxybenzofuran-2-yl)ethyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate
Reaction equation
[CH3:1][O:2][C:3]1[CH:37]=[CH:36][C:6]2[CH:7]=[C:8]([C:10]#[C:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:20]4([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22][CH2:21]4)=[CH:14][CH:13]=3)[O:9][C:5]=2[CH:4]=1.C(OC(=O)NC1(C#CC2C=CC(C#CCN3C4C(=CC=C(OC)C=4)C(C(=O)C4C=C(OC)C(OC)=C(OC)C=4)=C3)=CC=2)COC(C)(C)OC1)(C)(C)C>>[C:31]([O:30][C:29](=[O:35])[NH:28][C:20]1([CH2:19][CH2:18][C:15]2[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][C:8]3[O:9][C:5]4[CH:4]=[C:3]([O:2][CH3:1])[CH:37]=[CH:36][C:6]=4[CH:7]=3)=[CH:13][CH:14]=2)[CH2:21][O:22][C:23]([CH3:26])([CH3:27])[O:24][CH2:25]1)([CH3:32])([CH3:33])[CH3:34]Participants
3
Reactant 2
Product 1
Procedure
When the product of Step E was substituted for 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 in Example 14, Step D, the similar process afforded the title compound in 69%, as light creamy crystalline compound. 1H-NMR CDCl3) 1.40 (s, 3H); 1.42 (s, 3H); 1.46 (s, 9H); 1.92-2.03 (m, 2H); 2.49-2.55 (m, 2H); 2.99 (s, 4H); 3.65 (d, 2H, J=11.79 Hz); 3.83 (s, 3H); 3.87 (d, 2H, J=11.76 Hz); 4.94 (s, 1H); 6.25 (s, 1H); 6.80 (dd, 1H, J=2.24, 8.48 Hz); 6.97 (d, 1H), J=1.95 Hz); 7.09 (s, 4H); 7.30 (d, 2H, J=8.48 Hz).
Sources & evidence
- ORD record
- ord-621f1ebc89ff40328a4b0b1b45d83d8f
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181182B2
Reaction notes
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