Dimethylformamide → Ethyl 6-nitro-3-[(trimethylsilyl)ethynyl]-1-benzothiophene-2-carboxylate

HRID 1551623Notes

Reaction equation

HRID 1551623 reaction equation
[Br:12][c:13]1[c:14]([C:25](=[O:26])[O:27][CH2:28][CH3:29])[s:15][c:16]2[c:17]1[cH:18][cH:19][c:20]([N+:22](=[O:23])[O-:24])[cH:21]2.[CH3:6][Si:7]([CH3:8])([CH3:9])[C:10]#[CH:11].[CH3:73][CH2:74][N:75]([CH2:76][CH3:77])[CH2:78][CH3:79].[Cu:71][I:72].[O:1]=[CH:2][N:3]([CH3:4])[CH3:5].[Pd:30]([Cl:31])[Cl:32].[c:33]1([P:34]([c:35]2[cH:36][cH:37][cH:38][cH:39][cH:40]2)[c:41]2[cH:42][cH:43][cH:44][cH:45][cH:46]2)[cH:47][cH:48][cH:49][cH:50][cH:51]1.[c:52]1([P:53]([c:54]2[cH:55][cH:56][cH:57][cH:58][cH:59]2)[c:60]2[cH:61][cH:62][cH:63][cH:64][cH:65]2)[cH:66][cH:67][cH:68][cH:69][cH:70]1>>[CH3:6][Si:7]([CH3:8])([CH3:9])[C:10]#[C:11][c:13]1[c:14]([C:25](=[O:26])[O:27][CH2:28][CH3:29])[s:15][c:16]2[c:17]1[cH:18][cH:19][c:20]([N+:22](=[O:23])[O-:24])[cH:21]2

Participants

8

Reactant 7

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 66111TrimethylsilylacetyleneHCID 67549192Ethyl 3-bromo-6-nitro-1-benzothiophene-2-carboxylate

Product 1

HCID 67549085Ethyl 6-nitro-3-[(trimethylsilyl)ethynyl]-1-benzothiophene-2-carboxylate

Sources & evidence

ORD record
ord-44bee400da5645baa495111b65a9f97d
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (1/10)

Reaction notes

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