Tetrahydrofuran → Methyl 2-(2-fluorophenylamino)-3,4-difluoro-5-((trimethylsilyl)ethynyl)benzoate

HRID 154532Notes

Reaction equation

HRID 154532 reaction equation
[Br:1][c:2]1[c:3]([F:21])[c:4]([F:20])[c:5]([NH:12][c:13]2[c:14]([F:19])[cH:15][cH:16][cH:17][cH:18]2)[c:6]([C:7](=[O:8])[O:9][CH3:10])[cH:11]1.[CH2:28]1[O:29][CH2:30][CH2:31][CH2:32]1.[Cu:33][I:34].[Pd:35]([Cl:36])[Cl:37].[Si:22]([CH3:23])([CH3:24])([CH3:25])[C:26]#[CH:27].[c:38]1([P:39]([c:40]2[cH:41][cH:42][cH:43][cH:44][cH:45]2)[c:46]2[cH:47][cH:48][cH:49][cH:50][cH:51]2)[cH:52][cH:53][cH:54][cH:55][cH:56]1.[c:57]1([P:58]([c:59]2[cH:60][cH:61][cH:62][cH:63][cH:64]2)[c:65]2[cH:66][cH:67][cH:68][cH:69][cH:70]2)[cH:71][cH:72][cH:73][cH:74][cH:75]1>>[c:2]1([C:27]#[C:26][Si:22]([CH3:23])([CH3:24])[CH3:25])[c:3]([F:21])[c:4]([F:20])[c:5]([NH:12][c:13]2[c:14]([F:19])[cH:15][cH:16][cH:17][cH:18]2)[c:6]([C:7](=[O:8])[O:9][CH3:10])[cH:11]1

Participants

7

Reactant 6

HCID 8028TetrahydrofuranHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 66111TrimethylsilylacetyleneHCID 59519391Methyl 5-bromo-2-(2-fluorophenylamino)-3,4-difluorobenzoate

Product 1

HCID 59519400Methyl 2-(2-fluorophenylamino)-3,4-difluoro-5-((trimethylsilyl)ethynyl)benzoate

Sources & evidence

ORD record
ord-e9dd497c58a34eb898644fc6331286e7
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (9/10)

Reaction notes

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