Tetrahydrofuran → (4-{4-[4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)pent-1-ynyl]phenyl}but-3-ynyl)-carbamic acid benzyl ester

HRID 187909Notes

Reaction equation

HRID 187909 reaction equation
[CH2:1]([c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1)[O:8][C:9]([NH:10][CH2:11][CH2:12][C:13]#[C:14][c:15]1[cH:16][cH:17][c:18]([I:21])[cH:19][cH:20]1)=[O:22].[CH2:46]1[O:47][CH2:48][CH2:49][CH2:50]1.[CH3:23][CH2:24][N:25]([CH2:26][CH3:27])[CH2:28][CH3:29].[CH3:30][CH:31]([CH2:32][C:33]#[CH:34])[N:35]1[C:36](=[O:45])[c:37]2[cH:38][cH:39][cH:40][cH:41][c:42]2[C:43]1=[O:44].[Cu:51][I:52].[Pd:53]([Cl:54])[Cl:55].[c:56]1([P:57]([c:58]2[cH:59][cH:60][cH:61][cH:62][cH:63]2)[c:64]2[cH:65][cH:66][cH:67][cH:68][cH:69]2)[cH:70][cH:71][cH:72][cH:73][cH:74]1.[c:75]1([P:76]([c:77]2[cH:78][cH:79][cH:80][cH:81][cH:82]2)[c:83]2[cH:84][cH:85][cH:86][cH:87][cH:88]2)[cH:89][cH:90][cH:91][cH:92][cH:93]1>>[CH2:1]([c:2]1[cH:3][cH:4][cH:5][cH:6][cH:7]1)[O:8][C:9]([NH:10][CH2:11][CH2:12][C:13]#[C:14][c:15]1[cH:16][cH:17][c:18]([C:34]#[C:33][CH2:32][CH:31]([CH3:30])[N:35]2[C:36](=[O:45])[c:37]3[cH:38][cH:39][cH:40][cH:41][c:42]3[C:43]2=[O:44])[cH:19][cH:20]1)=[O:22]

Participants

8

Reactant 7

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 113333492-(1-Methylbut-3-ynyl)isoindole-1,3-dioneHCID 59750570Benzyl [4-(4-iodophenyl)but-3-yn-1-yl]carbamate

Product 1

HCID 66860631(4-{4-[4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)pent-1-ynyl]phenyl}but-3-ynyl)-carbamic acid benzyl ester

Sources & evidence

ORD record
ord-7dacc72378314836b24aeb1e0cb62f32
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (6/10)

Reaction notes

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