Dimethylformamide → 5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)-ethynyl]nicotinic acid

HRID 1535749Notes

Reaction equation

HRID 1535749 reaction equation
[Br:19][c:20]1[cH:21][n:22][cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28]1.[C:1](#[CH:2])[c:3]1[cH:4][c:5]([NH:9][C:10](=[O:11])[c:12]2[cH:13][c:14]([CH3:18])[n:15][n:16]2[CH3:17])[cH:6][cH:7][cH:8]1.[CH3:34][CH2:35][O:36][C:37]([CH3:38])=[O:39].[Cu:81][I:82].[O:29]=[CH:30][N:31]([CH3:32])[CH3:33].[Pd:40]([Cl:41])[Cl:42].[c:43]1([P:44]([c:45]2[cH:46][cH:47][cH:48][cH:49][cH:50]2)[c:51]2[cH:52][cH:53][cH:54][cH:55][cH:56]2)[cH:57][cH:58][cH:59][cH:60][cH:61]1.[c:62]1([P:63]([c:64]2[cH:65][cH:66][cH:67][cH:68][cH:69]2)[c:70]2[cH:71][cH:72][cH:73][cH:74][cH:75]2)[cH:76][cH:77][cH:78][cH:79][cH:80]1>>[C:1](#[C:2][c:20]1[cH:21][n:22][cH:23][c:24]([C:25](=[O:26])[OH:27])[cH:28]1)[c:3]1[cH:4][c:5]([NH:9][C:10](=[O:11])[c:12]2[cH:13][c:14]([CH3:18])[n:15][n:16]2[CH3:17])[cH:6][cH:7][cH:8]1

Participants

8

Reactant 7

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 887075-Bromonicotinic acidHCID 57657904N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

Product 1

HCID 576579595-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)-ethynyl]nicotinic acid

Sources & evidence

ORD record
ord-71a4a763976a4b72a77e33a2c92a6a60
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (1/10)

Reaction notes

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