Acetate → tert-butyl (1E,4E)-4-(dipropylcarbamoyl)-8-(4-hydroxyphenyl)-3H-benzo[b]azepin-2-ylcarbamate

HRID 1145790Notes

Reaction equation

HRID 1145790 reaction equation
[Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:29]1)[N:7]=[C:8]([NH:21][C:22]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:28])[CH2:9][C:10]([C:12]([N:13]([CH2:14][CH2:15][CH3:16])[CH2:17][CH2:18][CH3:19])=[O:20])=[CH:11]2.[CH3:85][CH2:86][OH:87].[K:41].[K:42].[Na+:70].[Na+:71].[O-:72][C:73](=[O:74])[O-:75].[O-:77][C:78]([CH3:79])=[O:80].[O-:81][C:82]([CH3:83])=[O:84].[OH2:40].[OH:30][c:31]1[cH:32][cH:33][c:34]([B:37]([OH:38])[OH:39])[cH:35][cH:36]1.[Pd+2:76].[c:43]1([P:44]([c:45]2[cH:46][cH:47][c:48]([S:49]([OH:50])(=[O:51])=[O:52])[cH:53][cH:54]2)[c:55]2[cH:56][cH:57][c:58]([S:59]([OH:60])(=[O:61])=[O:62])[cH:63][cH:64]2)[cH:65][cH:66][cH:67][cH:68][cH:69]1>>[c:2]1(-[c:34]2[cH:33][cH:32][c:31]([OH:30])[cH:36][cH:35]2)[cH:3][cH:4][c:5]2[c:6]([cH:29]1)[N:7]=[C:8]([NH:21][C:22]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:28])[CH2:9][C:10]([C:12]([N:13]([CH2:14][CH2:15][CH3:16])[CH2:17][CH2:18][CH3:19])=[O:20])=[CH:11]2

Participants

11

Reactant 10

HCID 175Acetate2×HCID 702EthanolHCID 923Sodium ion2×HCID 962WaterHCID 19660Carbonate IonHCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)HCID 27343604-Hydroxyphenylboronic acidHCID 43036894,4'-(Phenylphosphinidene)bis-benzenesulfonic acidHCID 5462222Potassium2×HCID 46928349tert-Butyl (8-bromo-4-(dipropylcarbamoyl)-3H-benzo[b]azepin-2-yl)carbamate

Product 1

HCID 86652679tert-butyl (1E,4E)-4-(dipropylcarbamoyl)-8-(4-hydroxyphenyl)-3H-benzo[b]azepin-2-ylcarbamate

Sources & evidence

ORD record
ord-f50ee11a02fa47b180e5b76eeab09297
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (7/10)

Reaction notes

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