Acetate → Ethyl 4-bromo-5-(3-cyano-5-fluorophenyl)thiophene-2-carboxylate

HRID 698351Notes

Reaction equation

HRID 698351 reaction equation
[Br:1][c:2]1[cH:3][c:4]([C:8](=[O:9])[O:10][CH2:11][CH3:12])[s:5][c:6]1[Br:7].[C:31](=[O:32])([O-:33])[O-:34].[CH3:71][O:72][CH2:73][CH2:74][O:75][CH3:76].[CH:37]1([P:38]([CH:39]2[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]2)[c:45]2[cH:46][cH:47][cH:48][cH:49][c:50]2-[c:51]2[c:52]([CH:53]([CH3:54])[CH3:55])[cH:56][c:57]([CH:58]([CH3:59])[CH3:60])[cH:61][c:62]2[CH:63]([CH3:64])[CH3:65])[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70]1.[Cs+:35].[Cs+:36].[F:13][c:14]1[cH:15][c:16]([C:29]#[N:30])[cH:17][c:18]([B:20]2[O:21][C:22]([CH3:23])([CH3:24])[C:25]([CH3:26])([CH3:27])[O:28]2)[cH:19]1.[O-:78][C:79]([CH3:80])=[O:81].[O-:82][C:83]([CH3:84])=[O:85].[OH2:86].[Pd+2:77]>>[Br:1][c:2]1[cH:3][c:4]([C:8](=[O:9])[O:10][CH2:11][CH3:12])[s:5][c:6]1-[c:18]1[cH:17][c:16]([C:29]#[N:30])[cH:15][c:14]([F:13])[cH:19]1

Participants

10

Reactant 9

HCID 175Acetate2×HCID 962WaterHCID 80711,2-DimethoxyethaneHCID 19660Carbonate IonHCID 104967Cesium cation2×HCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 15073982Ethyl 4,5-dibromothiophene-2-carboxylateHCID 467381943-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Product 1

HCID 66681595Ethyl 4-bromo-5-(3-cyano-5-fluorophenyl)thiophene-2-carboxylate

Sources & evidence

ORD record
ord-6c4944317d0e4713979c91031d40539a
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (3/10)

Reaction notes

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