Triethylamine → 3-Chloro-5-[2-(trimethylsilyl)ethynyl]pyridine

HRID 689744Notes

Reaction equation

HRID 689744 reaction equation
[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH3:7].[CH3:29][CH2:30][O:31][C:32](=[O:33])[CH3:34].[CH3:8][Si:9]([CH3:10])([CH3:11])[C:12]#[CH:13].[Cl:14][c:15]1[cH:16][c:17]([O:21][S:22]([C:23]([F:24])([F:25])[F:26])(=[O:27])=[O:28])[cH:18][n:19][cH:20]1.[Cu:76][I:77].[Pd:35]([Cl:36])[Cl: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>>[CH3:8][Si:9]([CH3:10])([CH3:11])[C:12]#[C:13][c:17]1[cH:16][c:15]([Cl:14])[cH:20][n:19][cH:18]1

Participants

8

Reactant 7

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 66111TrimethylsilylacetyleneHCID 151858705-Chloropyridin-3-yl trifluoromethanesulfonate

Product 1

HCID 235008913-Chloro-5-[2-(trimethylsilyl)ethynyl]pyridine

Sources & evidence

ORD record
ord-1b23d749eaf2411a8b05c0466b7af6ee
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (3/10)

Reaction notes

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