Acetate → 1-Phenylsulfonyl-5-trimethylsilylethynylindole

HRID 138818Notes

Reaction equation

HRID 138818 reaction equation
[Br:1][c:2]1[cH:3][c:4]2[cH:5][cH:6][n:7]([S:11](=[O:12])(=[O:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[c:8]2[cH:9][cH:10]1.[C:57]([O-:58])(=[O:59])[CH3:60].[C:62]([O-:63])(=[O:64])[CH3:65].[CH3:39][CH2:40][N:41]([CH2:42][CH3:43])[CH2:44][CH3:45].[CH3:46][Si:47]([CH3:48])([CH3:49])[C:50]#[CH:51].[CH3:67][CH2:68][O:69][C:70](=[O:71])[CH3:72].[CH3:73][N:74]([CH3:75])[CH:76]=[O:77].[O:52]1[CH2:53][CH2:54][CH2:55][CH2:56]1.[OH2:66].[Pd+2:61].[c:20]1([P:21]([c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[cH:34][cH:35][cH:36][cH:37][cH:38]1>>[c:2]1([C:51]#[C:50][Si:47]([CH3:46])([CH3:48])[CH3:49])[cH:3][c:4]2[cH:5][cH:6][n:7]([S:11](=[O:12])(=[O:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[c:8]2[cH:9][cH:10]1

Participants

11

Reactant 10

HCID 175Acetate2×HCID 962WaterHCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)HCID 27762101-(Benzenesulfonyl)-5-bromo-1H-indole

Product 1

HCID 227101661-Phenylsulfonyl-5-trimethylsilylethynylindole

Sources & evidence

ORD record
ord-220d11098a2c4e009771e4f39ab0471e
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (9/10)

Reaction notes

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