Tetrahydrofuran → 5-((4-Fluoro-3-formylphenyl)ethynyl)nicotinonitrile

HRID 2130912Notes

Reaction equation

HRID 2130912 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][N:27]([CH2:28][CH3:29])[CH2:30][CH3:31].[CH3:33][CH2:34][CH2:35][CH2:36][N+:37]([CH2:38][CH2:39][CH2:40][CH3:41])([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:46][CH2:47][CH2:48][CH3:49].[Cu:96][I:97].[F-:32].[F:15][c:16]1[c:17]([CH:18]=[O:19])[cH:20][c:21]([I:24])[cH:22][cH:23]1.[O:50]1[CH2:51][CH2:52][CH2:53][CH2:54]1.[Pd:55]([Cl:56])[Cl:57].[c:58]1([P:59]([c:60]2[cH:61][cH:62][cH:63][cH:64][cH:65]2)[c:66]2[cH:67][cH:68][cH:69][cH:70][cH:71]2)[cH:72][cH:73][cH:74][cH:75][cH:76]1.[c:77]1([P:78]([c:79]2[cH:80][cH:81][cH:82][cH:83][cH:84]2)[c:85]2[cH:86][cH:87][cH:88][cH:89][cH:90]2)[cH:91][cH:92][cH:93][cH:94][cH:95]1>>[C:5](#[C:6][c:7]1[cH:8][n:9][cH:10][c:11]([C:12]#[N:13])[cH:14]1)[c:21]1[cH:20][c:17]([CH:18]=[O:19])[c:16]([F:15])[cH:23][cH:22]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 161156995-[2-(Trimethylsilyl)ethynyl]pyridine-3-carbonitrileHCID 162170582-Fluoro-5-iodobenzaldehyde

Product 1

HCID 848197895-((4-Fluoro-3-formylphenyl)ethynyl)nicotinonitrile

Sources & evidence

ORD record
ord-cfebf9d99401414ea18cf1204e30a8ea
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (4/10)

Reaction notes

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