Water → Tert-butyl 4-(but-1-ynyl)-6-chloropyridin-3-ylcarbamate

HRID 291605

Reaction equation

HRID 291605 reaction equation
[C:1]([CH3:2])([CH3:3])([CH3:4])[O:5][C:6]([NH:7][c:8]1[cH:9][n:10][c:11]([Cl:15])[cH:12][c:13]1[I:14])=[O:16].[CH3:21][CH2:22][N:23]([CH2:24][CH3:25])[CH2:26][CH3:27].[CH3:28][c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1.[CH:17]#[C:18][CH2:19][CH3:20].[Cu:36][I:37].[OH2:35].[Pd:38]([Cl:39])[Cl:40].[c:41]1([P:42]([c:43]2[cH:44][cH:45][cH:46][cH:47][cH:48]2)[c:49]2[cH:50][cH:51][cH:52][cH:53][cH:54]2)[cH:55][cH:56][cH:57][cH:58][cH:59]1.[c:60]1([P:61]([c:62]2[cH:63][cH:64][cH:65][cH:66][cH:67]2)[c:68]2[cH:69][cH:70][cH:71][cH:72][cH:73]2)[cH:74][cH:75][cH:76][cH:77][cH:78]1>>[C:1]([CH3:2])([CH3:3])([CH3:4])[O:5][C:6]([NH:7][c:8]1[cH:9][n:10][c:11]([Cl:15])[cH:12][c:13]1[C:17]#[C:18][CH2:19][CH3:20])=[O:16]

Participants

9

Reactant 8

HCID 962WaterHCID 1140TolueneHCID 78461-ButyneHCID 8471TriethylamineHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 53415320tert-Butyl (6-chloro-4-iodopyridin-3-yl)carbamate

Product 1

HCID 57908177Tert-butyl 4-(but-1-ynyl)-6-chloropyridin-3-ylcarbamate

Sources & evidence

ORD record
ord-1c8e2aae999b4d10906b09b78dc47900
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (8/10)

Linked notes

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