Water → 3-Bromo-5-(prop-1-yn-1-yl)pyridine

HRID 662427Notes

Reaction equation

HRID 662427 reaction equation
[Br:1][c:2]1[cH:3][n:4][cH:5][c:6]([Br:7])[cH:8]1.[CH2:24]([N+:25]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:34][CH2:35][CH2:36][CH3:37])[CH2:38][CH2:39][CH3:40].[CH3:16][CH2:17][N:18]([CH2:19][CH3:20])[CH2:21][CH3:22].[CH3:41][c:42]1[cH:43][cH:44][cH:45][cH:46][cH:47]1.[CH3:9][Si:10]([C:11]#[C:12][CH3:13])([CH3:14])[CH3:15].[Cu:48][I:49].[F-:23].[OH2:127].[cH:50]1[cH:51][cH:52][c:53]([P:54]([Pd:55]([P:56]([c:57]2[cH:58][cH:59][cH:60][cH:61][cH:62]2)([c:63]2[cH:64][cH:65][cH:66][cH:67][cH:68]2)[c:69]2[cH:70][cH:71][cH:72][cH:73][cH:74]2)([P:75]([c:76]2[cH:77][cH:78][cH:79][cH:80][cH:81]2)([c:82]2[cH:83][cH:84][cH:85][cH:86][cH:87]2)[c:88]2[cH:89][cH:90][cH:91][cH:92][cH:93]2)[P:94]([c:95]2[cH:96][cH:97][cH:98][cH:99][cH:100]2)([c:101]2[cH:102][cH:103][cH:104][cH:105][cH:106]2)[c:107]2[cH:108][cH:109][cH:110][cH:111][cH:112]2)([c:113]2[cH:114][cH:115][cH:116][cH:117][cH:118]2)[c:119]2[cH:120][cH:121][cH:122][cH:123][cH:124]2)[cH:125][cH:126]1>>[c:2]1([C:11]#[C:12][CH3:13])[cH:3][n:4][cH:5][c:6]([Br:7])[cH:8]1

Participants

10

Reactant 9

HCID 962WaterHCID 1140TolueneHCID 8471TriethylamineHCID 16028TetrabutylammoniumHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 28179Fluoride IonHCID 693693,5-DibromopyridineHCID 803631-(Trimethylsilyl)prop-1-yneHCID 178420554HCID 178420554, compound

Product 1

HCID 574665963-Bromo-5-(prop-1-yn-1-yl)pyridine

Sources & evidence

ORD record
ord-4544ac2cc858456ca9db26ab0fc1bdf6
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (3/10)

Reaction notes

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