Acetate → 4-[4-(Tert-butyldimethylsiloxy)piperidin-1-yl]benzonitrile

HRID 2147349Notes

Reaction equation

HRID 2147349 reaction equation
[Br:1][c:2]1[cH:3][cH:4][c:5]([C:6]#[N:7])[cH:8][cH:9]1.[C:10]([CH3:11])([CH3:12])([CH3:13])[Si:14]([O:15][CH:16]1[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]1)([CH3:22])[CH3:23].[C:83]([O-:84])(=[O:85])[CH3:86].[C:88]([O-:89])(=[O:90])[CH3:91].[CH3:70][C:71]([CH3:72])([O-:73])[CH3:74].[CH3:76][c:77]1[cH:78][cH:79][cH:80][cH:81][cH:82]1.[CH3:92][CH2:93][O:94][C:95](=[O:96])[CH3:97].[Na+:75].[Pd+2:87].[cH:24]1[cH:25][cH:26][c:27]([P:28]([c:29]2[cH:30][cH:31][c:32]3[c:33]([cH:34][cH:35][cH:36][cH:37]3)[c:38]2-[c:39]2[c:40]3[c:41]([cH:42][cH:43][cH:44][cH:45]3)[cH:46][cH:47][c:48]2[P:49]([c:50]2[cH:51][cH:52][cH:53][cH:54][cH:55]2)[c:56]2[cH:57][cH:58][cH:59][cH:60][cH:61]2)[c:62]2[cH:63][cH:64][cH:65][cH:66][cH:67]2)[cH:68][cH:69]1>>[c:2]1([N:19]2[CH2:18][CH2:17][CH:16]([O:15][Si:14]([C:10]([CH3:11])([CH3:12])[CH3:13])([CH3:22])[CH3:23])[CH2:21][CH2:20]2)[cH:3][cH:4][c:5]([C:6]#[N:7])[cH:8][cH:9]1

Participants

10

Reactant 9

HCID 175Acetate2×HCID 923Sodium ionHCID 1140TolueneHCID 8857Ethyl AcetateHCID 12162Benzonitrile, 4-bromo-HCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)HCID 634876Binap, (A+-)-HCID 45749132-Methylpropan-2-olateHCID 114813284-((Tert-butyldimethylsilyl)oxy)piperidine

Product 1

HCID 694805284-[4-(Tert-butyldimethylsiloxy)piperidin-1-yl]benzonitrile

Sources & evidence

ORD record
ord-60efa6691faa4d0ea90d796a33831980
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (4/10)

Reaction notes

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