Piperidine → Trifluoro-methanesulfonic acid 1-(4-trimethylsilanylethynyl-phenyl)-1H-indol-5-yl ester

HRID 211952Notes

Reaction equation

HRID 211952 reaction equation
[Br:1][c:2]1[cH:3][cH:4][c:5](-[n:8]2[cH:9][cH:10][c:11]3[cH:12][c:13]([O:17][S:18](=[O:19])(=[O:20])[C:21]([F:22])([F:23])[F:24])[cH:14][cH:15][c:16]23)[cH:6][cH:7]1.[C:25](#[CH:26])[Si:27]([CH3:28])([CH3:29])[CH3:30].[CH2:31]1[CH2:32][CH2:33][NH:34][CH2:35][CH2:36]1.[Cu:114][I:115].[Pd:37].[c:38]1([P:39]([c:40]2[cH:41][cH:42][cH:43][cH:44][cH:45]2)[c:46]2[cH:47][cH:48][cH:49][cH:50][cH:51]2)[cH:52][cH:53][cH:54][cH:55][cH:56]1.[c:57]1([P:58]([c:59]2[cH:60][cH:61][cH:62][cH:63][cH:64]2)[c:65]2[cH:66][cH:67][cH:68][cH:69][cH:70]2)[cH:71][cH:72][cH:73][cH:74][cH:75]1.[c:76]1([P:77]([c:78]2[cH:79][cH:80][cH:81][cH:82][cH:83]2)[c:84]2[cH:85][cH:86][cH:87][cH:88][cH:89]2)[cH:90][cH:91][cH:92][cH:93][cH:94]1.[c:95]1([P:96]([c:97]2[cH:98][cH:99][cH:100][cH:101][cH:102]2)[c:103]2[cH:104][cH:105][cH:106][cH:107][cH:108]2)[cH:109][cH:110][cH:111][cH:112][cH:113]1>>[c:2]1([C:26]#[C:25][Si:27]([CH3:28])([CH3:29])[CH3:30])[cH:3][cH:4][c:5](-[n:8]2[cH:9][cH:10][c:11]3[cH:12][c:13]([O:17][S:18](=[O:19])(=[O:20])[C:21]([F:22])([F:23])[F:24])[cH:14][cH:15][c:16]23)[cH:6][cH:7]1

Participants

7

Reactant 6

HCID 8082PiperidineHCID 11776Triphenylphosphine4×HCID 23938PalladiumHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 66111TrimethylsilylacetyleneHCID 86585588HCID 86585588, compound

Product 1

HCID 86585591Trifluoro-methanesulfonic acid 1-(4-trimethylsilanylethynyl-phenyl)-1H-indol-5-yl ester

Sources & evidence

ORD record
ord-91dc49ab70e6467cb80d855594a3dea3
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (6/10)

Reaction notes

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