1-Octyne → 5-((2'-(Trifluoromethyl)biphenyl-4-yl)ethynyl)-1H-indole

HRID 710444

Reaction equation

HRID 710444 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([F:18])([F:17])[F:16])=[CH:5][CH:4]=1)#[CH:2].C#CCCCCCC.I[C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][CH:32]=[CH:31]2.IC1C=C2C(=CC=1)CN(C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C2>>[F:18][C:15]([F:16])([F:17])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([C:1]#[C:2][C:28]2[CH:29]=[C:30]3[C:34](=[CH:35][CH:36]=2)[NH:33][CH:32]=[CH:31]3)=[CH:4][CH:5]=1

Participants

5

Reactant 4

HCID 123701-OctyneHCID 27823135-Iodo-1H-indoleHCID 667262485-Iodo-2-tritylisoindolineHCID 866618064'-Ethynyl-2-(trifluoromethyl)biphenyl

Product 1

HCID 667267875-((2'-(Trifluoromethyl)biphenyl-4-yl)ethynyl)-1H-indoleYield 86%

Procedure

When the product of Step A was substituted for 1-octyne and 5-iodoindole was substituted for 5-iodo-2-tritylisoindoline in Example 2, Step D, the similar process afforded the title compound in 86% yield, as a colourless paste. 1H-NMR (CDCl3) 7.56 (broad s, 1H); 7.28-7.4 (m, 5H); 7.46 (tr, 1H, J=7.25 Hz); 7.53-7.58 (m, 3H); 7.73 (d, 1H, J=7.85 Hz); 7.87 (s, 1H); 8.23 (broad s, 1H).

Sources & evidence

ORD record
ord-ff943ebbc5264be787413209da71d288
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Linked notes

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