Benzonitrile → 1-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-[4-(1-phenyl-3-trimethylsilyl-prop-2-ynylidene)-1-piperidyl]ethane-1,2-dione

HRID 1121613Notes

Reaction equation

HRID 1121613 reaction equation
[Br:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)=[C:9]1[CH2:10][CH2:11][N:12]([C:15]([C:16](=[O:17])[c:18]2[cH:19][nH:20][c:21]3[c:22]([O:29][CH3:30])[n:23][cH:24][c:25]([O:27][CH3:28])[c:26]23)=[O:31])[CH2:13][CH2:14]1.[C:47]([c:48]1[cH:49][cH:50][cH:51][cH:52][cH:53]1)#[N:54].[C:55]([c:56]1[cH:57][cH:58][cH:59][cH:60][cH:61]1)#[N:62].[CH2:38]1[CH2:39][CH2:40][NH:41][CH2:42][CH2:43]1.[CH3:32][Si:33]([CH3:34])([CH3:35])[C:36]#[CH:37].[Cl:44][Pd:45][Cl:46].[Cu:63][I:64]>>[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)(=[C:9]1[CH2:10][CH2:11][N:12]([C:15]([C:16](=[O:17])[c:18]2[cH:19][nH:20][c:21]3[c:22]([O:29][CH3:30])[n:23][cH:24][c:25]([O:27][CH3:28])[c:26]23)=[O:31])[CH2:13][CH2:14]1)[C:37]#[C:36][Si:33]([CH3:32])([CH3:34])[CH3:35]

Participants

7

Reactant 6

HCID 7505Benzonitrile2×HCID 8082PiperidineHCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 66111TrimethylsilylacetyleneHCID 5279817Piperidine, 4-(bromophenylmethylene)-1-[2-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-1,2-dioxoethyl]-

Product 1

HCID 52799201-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-[4-(1-phenyl-3-trimethylsilyl-prop-2-ynylidene)-1-piperidyl]ethane-1,2-dione

Sources & evidence

ORD record
ord-96b17d51aa244087ab5bdf0c8cdb1ba4
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (7/10)

Reaction notes

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