Toluene → Ethyl 2-ethynyl-4-methylthiazole-5-carboxylate

HRID 196427Notes

Reaction equation

HRID 196427 reaction equation
[Br:1][c:2]1[s:3][c:4]([C:8](=[O:9])[O:10][CH2:11][CH3:12])[c:5]([CH3:7])[n:6]1.[CH3:22][Si:23]([C:24]#[CH:25])([CH3:26])[CH3:27].[CH3:28][c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1.[CH:13]([CH3:14])([N:15]([CH2:16][CH3:17])[CH:18]([CH3:19])[CH3:20])[CH3:21].[Cu:35][I:36].[Pd:37]([Cl:38])[Cl:39].[c:40]1([P:41]([c:42]2[cH:43][cH:44][cH:45][cH:46][cH:47]2)[c:48]2[cH:49][cH:50][cH:51][cH:52][cH:53]2)[cH:54][cH:55][cH:56][cH:57][cH:58]1.[c:59]1([P:60]([c:61]2[cH:62][cH:63][cH:64][cH:65][cH:66]2)[c:67]2[cH:68][cH:69][cH:70][cH:71][cH:72]2)[cH:73][cH:74][cH:75][cH:76][cH:77]1>>[c:2]1([C:13]#[CH:14])[s:3][c:4]([C:8](=[O:9])[O:10][CH2:11][CH3:12])[c:5]([CH3:7])[n:6]1

Participants

8

Reactant 7

HCID 1140TolueneHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 59179676Ethyl 2-ethynyl-4-methylthiazole-5-carboxylate

Sources & evidence

ORD record
ord-5159c62eee214c31be982020eb645419
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (6/10)

Reaction notes

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