Dimethylformamide → Tert-butyl 2-[3-[(4-chlorophenyl)methylcarbamoyl]-6-(3-hydroxyprop-1-ynyl)-4-oxo-1-quinolyl]acetate

HRID 108558Notes

Reaction equation

HRID 108558 reaction equation
[CH2:32]([NH:33][CH2:34][CH3:35])[CH3:36].[CH2:37]([C:38]#[CH:39])[OH:40].[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][C:8](=[O:9])[c:10]2[cH:11][n:12]([CH2:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[c:13]3[cH:14][cH:15][c:16]([I:21])[cH:17][c:18]3[c:19]2=[O:20])[cH:30][cH:31]1.[Cu:46][I:47].[O:41]=[CH:42][N:43]([CH3:44])[CH3:45].[Pd:48]([Cl:49])[Cl:50].[c:51]1([P:52]([c:53]2[cH:54][cH:55][cH:56][cH:57][cH:58]2)[c:59]2[cH:60][cH:61][cH:62][cH:63][cH:64]2)[cH:65][cH:66][cH:67][cH:68][cH:69]1.[c:70]1([P:71]([c:72]2[cH:73][cH:74][cH:75][cH:76][cH:77]2)[c:78]2[cH:79][cH:80][cH:81][cH:82][cH:83]2)[cH:84][cH:85][cH:86][cH:87][cH:88]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][C:8](=[O:9])[c:10]2[cH:11][n:12]([CH2:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[c:13]3[cH:14][cH:15][c:16]([C:39]#[C:38][CH2:37][OH:40])[cH:17][c:18]3[c:19]2=[O:20])[cH:30][cH:31]1

Participants

8

Reactant 7

HCID 6228DimethylformamideHCID 7859Propargyl alcoholHCID 8021DiethylamineHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 21192561tert-butyl 2-[3-{[(4-chlorobenzyl)amino]carbonyl}-6-iodo-4-oxo-1(4H)-quinolinyl]acetate

Product 1

HCID 16073847Tert-butyl 2-[3-[(4-chlorophenyl)methylcarbamoyl]-6-(3-hydroxyprop-1-ynyl)-4-oxo-1-quinolyl]acetate

Sources & evidence

ORD record
ord-3aa2790cd0e749ebafedd0211826c7cf
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (2/10)

Reaction notes

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