Ethanol → AZD4694 Precursor

HRID 1541291Notes

Reaction equation

HRID 1541291 reaction equation
[BH:1]([OH:2])[OH:3].[C:18]([CH3:19])([CH3:20])([CH3:21])[O:22][C:23]([N:24]([CH3:25])[c:26]1[n:27][c:28]([N+:33](=[O:34])[O-:35])[c:29]([Br:32])[cH:30][cH:31]1)=[O:36].[CH2:4]([CH3:5])[O:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14][cH:15][o:16]2)[cH:17]1.[CH3:37][CH2:38][N:39]([CH2:40][CH3:41])[CH2:42][CH3:43].[CH3:44][CH2:45][OH:46].[Pd:47]([Cl:48])[Cl:49].[c:50]1([P:51]([c:52]2[cH:53][cH:54][cH:55][cH:56][cH:57]2)[c:58]2[cH:59][cH:60][cH:61][cH:62][cH:63]2)[cH:64][cH:65][cH:66][cH:67][cH:68]1.[c:69]1([P:70]([c:71]2[cH:72][cH:73][cH:74][cH:75][cH:76]2)[c:77]2[cH:78][cH:79][cH:80][cH:81][cH:82]2)[cH:83][cH:84][cH:85][cH:86][cH:87]1>>[CH2:4]([CH3:5])[O:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([cH:14][c:15](-[c:29]3[c:28]([N+:33](=[O:34])[O-:35])[n:27][c:26]([N:24]([C:23]([O:22][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:36])[CH3:25])[cH:31][cH:30]3)[o:16]2)[cH:17]1

Participants

8

Reactant 7

HCID 702EthanolHCID 8471TriethylamineHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 61668Boronic AcidHCID 46183971(5-Bromo-6-nitro-pyridin-2-yl)-methyl-carbamic acid tert-butyl esterHCID 592274505-Ethoxymethoxy-benzofuran

Product 1

HCID 46183972AZD4694 Precursor

Sources & evidence

ORD record
ord-3f12a2bb6fc64b69b8784c667454319f
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (1/10)

Reaction notes

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