1-Octyne → Tert-butyl-2,2-dimethyl-5-((3-((3,4,5-trimethoxyphenyl)ethynyl)-phenyl)ethynyl)-1,3-dioxan-5-ylcarbamate

HRID 710347Notes

Reaction equation

HRID 710347 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]#[CH:14])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C#CCCCCCC.I[C:24]1[CH:25]=[C:26]([C:30]#[C:31][C:32]2([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:37][O:36][C:35]([CH3:39])([CH3:38])[O:34][CH2:33]2)[CH:27]=[CH:28][CH:29]=1.IC1C=C2C(=CC=1)CN(C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C2>>[C:43]([O:42][C:41](=[O:47])[NH:40][C:32]1([C:31]#[C:30][C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([C:14]#[C:13][C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:25]=2)[CH2:33][O:34][C:35]([CH3:39])([CH3:38])[O:36][CH2:37]1)([CH3:44])([CH3:45])[CH3:46]

Participants

5

Reactant 4

HCID 123701-OctyneHCID 118302605-Ethynyl-1,2,3-trimethoxybenzeneHCID 667262485-Iodo-2-tritylisoindolineHCID 66726793Tert-butyl 5-((3-iodophenyl)ethynyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Product 1

HCID 131733948Tert-butyl-2,2-dimethyl-5-((3-((3,4,5-trimethoxyphenyl)ethynyl)-phenyl)ethynyl)-1,3-dioxan-5-ylcarbamateYield 64%

Procedure

When 3,4,5-trimethoxyphenyl-acetylene was substituted for 1-octyne and the product of Step A was substituted for 5-iodo-2-tritylisoindoline in Example 2, Step D, the similar process afforded the title compound in 64% yield, as pale paste. 1H-NMR (CDCl3) 1.43 (s, 3H); 1.47 (s, 9H); 1.49 (5, 3H); 3.84 (s, 3H); 3.87 (s, 6H); 4.00 (d, 2H, J=11.4 Hz); 4.10 (d, 2H, J=11.33 Hz); 5.19 (broad s, 1H), 6.74 (s, 2H); 6.74-6.76 (m, 1H); 7.26-7.38 (m, 1H); 7.43 (d, 1H, J=7.67 Hz); 7.60 (broad s, 1H).

Sources & evidence

ORD record
ord-80871b0c478348aea607a94c06530118
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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