Tetrahydrofuran → 5-((Trimethylsilyl)ethynyl)picolinaldehyde

HRID 1575927Notes

Reaction equation

HRID 1575927 reaction equation
[Br:1][c:2]1[cH:3][cH:4][c:5]([CH:8]=[O:9])[n:6][cH:7]1.[CH2:42]1[O:43][CH2:44][CH2:45][CH2:46]1.[CH3:16][CH2:17][N:18]([CH2:19][CH3:20])[CH2:21][CH3:22].[CH3:91][CH2:92][O:93][C:94](=[O:95])[CH3:96].[Cu:47]([I:48])[I:49].[Pd:50]([Cl:51])[Cl:52].[Si:10]([CH3:11])([CH3:12])([CH3:13])[C:14]#[CH:15].[c:23]1([P:24]([c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[c:31]2[cH:32][cH:33][cH:34][cH:35][cH:36]2)[cH:37][cH:38][cH:39][cH:40][cH:41]1.[c:53]1([P:54]([c:55]2[cH:56][cH:57][cH:58][cH:59][cH:60]2)[c:61]2[cH:62][cH:63][cH:64][cH:65][cH:66]2)[cH:67][cH:68][cH:69][cH:70][cH:71]1.[c:72]1([P:73]([c:74]2[cH:75][cH:76][cH:77][cH:78][cH:79]2)[c:80]2[cH:81][cH:82][cH:83][cH:84][cH:85]2)[cH:86][cH:87][cH:88][cH:89][cH:90]1>>[c:2]1([C:15]#[C:14][Si:10]([CH3:11])([CH3:12])[CH3:13])[cH:3][cH:4][c:5]([CH:8]=[O:9])[n:6][cH:7]1

Participants

9

Reactant 8

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11776Triphenylphosphine3×HCID 24290Palladium ChlorideHCID 66111TrimethylsilylacetyleneHCID 83717Copper iodideHCID 98775625-Bromopyridine-2-carbaldehyde

Product 1

HCID 114014485-((Trimethylsilyl)ethynyl)picolinaldehyde

Sources & evidence

ORD record
ord-de076c4303634798a8b7ab4467ebc117
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (1/10)

Reaction notes

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