Dimethylformamide → methyl 6-amino-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]nicotinate

HRID 1227650Notes

Reaction equation

HRID 1227650 reaction equation
[C:13](#[CH:14])[c:15]1[cH:16][c:17]([NH:21][C:22](=[O:23])[c:24]2[cH:25][c:26]([CH3:30])[n:27][n:28]2[CH3:29])[cH:18][cH:19][cH:20]1.[CH3:31][CH2:32][N:33]([CH2:34][CH3:35])[CH2:36][CH3:37].[Cu:103][I:104].[NH2:1][c:2]1[n:3][cH:4][c:5]([C:6](=[O:7])[O:8][CH3:9])[cH:10][c:11]1[I:12].[O:57]=[CH:58][N:59]([CH3:60])[CH3:61].[Pd:62]([Cl:63])[Cl:64].[c:38]1([P:39]([c:40]2[cH:41][cH:42][cH:43][cH:44][cH:45]2)[c:46]2[cH:47][cH:48][cH:49][cH:50][cH:51]2)[cH:52][cH:53][cH:54][cH:55][cH:56]1.[c:65]1([P:66]([c:67]2[cH:68][cH:69][cH:70][cH:71][cH:72]2)[c:73]2[cH:74][cH:75][cH:76][cH:77][cH:78]2)[cH:79][cH:80][cH:81][cH:82][cH:83]1.[c:84]1([P:85]([c:86]2[cH:87][cH:88][cH:89][cH:90][cH:91]2)[c:92]2[cH:93][cH:94][cH:95][cH:96][cH:97]2)[cH:98][cH:99][cH:100][cH:101][cH:102]1>>[NH2:1][c:2]1[n:3][cH:4][c:5]([C:6](=[O:7])[O:8][CH3:9])[cH:10][c:11]1[C:14]#[C:13][c:15]1[cH:16][c:17]([NH:21][C:22](=[O:23])[c:24]2[cH:25][c:26]([CH3:30])[n:27][n:28]2[CH3:29])[cH:18][cH:19][cH:20]1

Participants

8

Reactant 7

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 11776Triphenylphosphine3×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 15350913Methyl 6-amino-5-iodopyridine-3-carboxylateHCID 57657904N-(3-ethynylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

Product 1

HCID 57657963methyl 6-amino-5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]nicotinate

Sources & evidence

ORD record
ord-c65d1327d518461abcbc4defc5acad5f
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (5/10)

Reaction notes

Loading…