Toluene → 4-{2-[2-(2,4-Difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulen-9-yl}-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

HRID 1236773Notes

Reaction equation

HRID 1236773 reaction equation
[B-:65]([F:66])([F:67])([F:68])[F:69].[Br:37][c:38]1[cH:39][cH:40][c:41]2[c:42]([cH:64]1)-[c:43]1[n:44][n:45](-[c:51]3[n:52](-[c:56]4[c:57]([F:63])[cH:58][c:59]([F:62])[cH:60][cH:61]4)[n:53][cH:54][n:55]3)[cH:46][c:47]1[CH2:48][CH2:49][O:50]2.[C:19](=[O:20])([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[N:26]1[CH2:27][CH2:28][CH:29]([C:32](=[O:33])[O:34][CH2:35][CH3:36])[CH2:30][CH2:31]1.[C:70]([PH+:71]([C:72]([CH3:73])([CH3:74])[CH3:75])[C:76]([CH3:77])([CH3:78])[CH3:79])([CH3:80])([CH3:81])[CH3:82].[CH2:14]([Li:15])[CH2:16][CH2:17][CH3:18].[CH3:83][c:84]1[cH:85][cH:86][cH:87][cH:88][cH:89]1.[CH:109](=[CH:110][C:111]([CH:112]=[CH:113][c:114]1[cH:115][cH:116][cH:117][cH:118][cH:119]1)=[O:120])[c:121]1[cH:122][cH:123][cH:124][cH:125][cH:126]1.[CH:1]1([NH:2][CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1.[CH:91](=[CH:92][C:93]([CH:94]=[CH:95][c:96]1[cH:97][cH:98][cH:99][cH:100][cH:101]1)=[O:102])[c:103]1[cH:104][cH:105][cH:106][cH:107][cH:108]1.[Pd:90]>>[C:19](=[O:20])([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[N:26]1[CH2:27][CH2:28][C:29]([C:32](=[O:33])[O:34][CH2:35][CH3:36])([c:38]2[cH:39][cH:40][c:41]3[c:42]([cH:64]2)-[c:43]2[n:44][n:45](-[c:51]4[n:52](-[c:56]5[c:57]([F:63])[cH:58][c:59]([F:62])[cH:60][cH:61]5)[n:53][cH:54][n:55]4)[cH:46][c:47]2[CH2:48][CH2:49][O:50]3)[CH2:30][CH2:31]1

Participants

10

Reactant 9

HCID 1140TolueneHCID 7582DicyclohexylamineHCID 23938PalladiumHCID 26255TetrafluoroborateHCID 95417Dibenzylidene acetone2×HCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylateHCID 4060964Tri-t-butylphosphoniumHCID 582044889-bromo-2-[2-(2,4-difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azuleneHCID 178418339Butyllithium

Product 1

HCID 582046194-{2-[2-(2,4-Difluoro-phenyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulen-9-yl}-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

Sources & evidence

ORD record
ord-83f7afe388604d6e88ed44f096ff8051
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (5/10)

Reaction notes

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