Tetrahydrofuran → 5-(3-Chloro-4-fluorophenylethynyl)-nicotinonitrile

HRID 110178Notes

Reaction equation

HRID 110178 reaction equation
[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][c:7]1[cH:8][n:9][cH:10][c:11]([C:12]#[N:13])[cH:14]1.[CH3:25][CH2:26][CH2:27][CH2:28][N+:29]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:38][CH2:39][CH2:40][CH3:41].[CH3:42][CH2:43][N:44]([CH2:45][CH3:46])[CH2:47][CH3:48].[Cl:15][c:16]1[c:17]([F:23])[cH:18][cH:19][c:20]([I:22])[cH:21]1.[Cu:95][I:96].[F-:24].[O:49]1[CH2:50][CH2:51][CH2:52][CH2:53]1.[Pd:54]([Cl:55])[Cl:56].[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:76]1([P:77]([c:78]2[cH:79][cH:80][cH:81][cH:82][cH:83]2)[c:84]2[cH:85][cH:86][cH:87][cH:88][cH:89]2)[cH:90][cH:91][cH:92][cH:93][cH:94]1>>[C:5](#[C:6][c:7]1[cH:8][n:9][cH:10][c:11]([C:12]#[N:13])[cH:14]1)[c:20]1[cH:19][cH:18][c:17]([F:23])[c:16]([Cl:15])[cH:21]1

Participants

10

Reactant 9

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 11776Triphenylphosphine2×HCID 16028TetrabutylammoniumHCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 28179Fluoride IonHCID 27246052-Chloro-1-fluoro-4-iodobenzeneHCID 161156995-[2-(Trimethylsilyl)ethynyl]pyridine-3-carbonitrile

Product 1

HCID 670478735-(3-Chloro-4-fluorophenylethynyl)-nicotinonitrile

Sources & evidence

ORD record
ord-4fefcee931814199a8248cd553e6deaf
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (2/10)

Reaction notes

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