Dimethylformamide → 2-Chloro-5-[(2-methyl-4-thiazolyl)ethynyl]pyridine

HRID 173251Notes

Reaction equation

HRID 173251 reaction equation
[CH3:21][CH2:22][N:23]([CH2:24][CH3:25])[CH2:26][CH3:27].[CH3:29][CH2:30][CH2:31][CH2:32][N+:33]([CH2:34][CH2:35][CH2:36][CH3:37])([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:42][CH2:43][CH2:44][CH3:45].[CH3:9][c:10]1[s:11][cH:12][c:13]([C:15]#[C:16][Si:17]([CH3:18])([CH3:19])[CH3:20])[n:14]1.[Cl:1][c:2]1[n:3][cH:4][c:5]([I:8])[cH:6][cH:7]1.[Cu:87][I:88].[F-:28].[O:89]=[CH:90][N:91]([CH3:92])[CH3:93].[Pd:46]([Cl:47])[Cl:48].[c:49]1([P:50]([c:51]2[cH:52][cH:53][cH:54][cH:55][cH:56]2)[c:57]2[cH:58][cH:59][cH:60][cH:61][cH:62]2)[cH:63][cH:64][cH:65][cH:66][cH:67]1.[c:68]1([P:69]([c:70]2[cH:71][cH:72][cH:73][cH:74][cH:75]2)[c:76]2[cH:77][cH:78][cH:79][cH:80][cH:81]2)[cH:82][cH:83][cH:84][cH:85][cH:86]1>>[Cl:1][c:2]1[n:3][cH:4][c:5]([C:16]#[C:15][c:13]2[cH:12][s:11][c:10]([CH3:9])[n:14]2)[cH:6][cH:7]1

Participants

10

Reactant 9

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 11776Triphenylphosphine2×HCID 16028TetrabutylammoniumHCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 28179Fluoride IonHCID 43971762-Chloro-5-iodopyridineHCID 109214422-Methyl-4-(2-(trimethylsilyl)ethynyl)-1,3-thiazole

Product 1

HCID 115649112-Chloro-5-[(2-methyl-4-thiazolyl)ethynyl]pyridine

Sources & evidence

ORD record
ord-98ad7d88da41479b9a0254b252c0ff51
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (9/10)

Reaction notes

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