Acetate → 5-[4-(4-methoxypyridin-3-yl)benzyl]-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester
Reaction equation
[C:31]([CH3:32])([CH3:33])([CH3:34])[O:35][C:36](=[O:37])[N:38]1[CH2:39][CH2:40][c:41]2[cH:42][c:43]3[c:47]([cH:48][c:49]2[CH:50]1[CH2:51][c:52]1[cH:53][cH:54][c:55]([Br:56])[cH:57][cH:58]1)[O:46][CH2:45][O:44]3.[C:89](=[O:90])([O-:91])[O-:92].[CH3:3][O:4][c:5]1[c:6](-[c:11]2[cH:12][cH:13][c:14]([CH2:15][CH:16]3[NH:17][CH2:18][CH2:19][c:20]4[cH:21][c:22]5[c:23]([cH:24][c:25]43)[O:26][CH2:27][O:28]5)[cH:29][cH:30]2)[cH:7][n:8][cH:9][cH:10]1.[CH3:59][O:60][c:61]1[cH:62][cH:63][n:64][cH:65][c:66]1[B:67]([OH:68])[OH:69].[CH3:95][CH:96]([OH:97])[CH3:98].[ClH:1].[ClH:2].[Na+:93].[Na+:94].[O-:100][C:101]([CH3:102])=[O:103].[O-:104][C:105]([CH3:106])=[O:107].[Pd+2:99].[c:70]1([P:71]([c:72]2[cH:73][cH:74][cH:75][cH:76][cH:77]2)[c:78]2[cH:79][cH:80][cH:81][cH:82][cH:83]2)[cH:84][cH:85][cH:86][cH:87][cH:88]1>>[CH3:3][O:4][c:5]1[c:6](-[c:11]2[cH:12][cH:13][c:14]([CH2:15][CH:16]3[N:17]([C:36]([O:35][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:37])[CH2:18][CH2:19][c:20]4[cH:21][c:22]5[c:23]([cH:24][c:25]43)[O:26][CH2:27][O:28]5)[cH:29][cH:30]2)[cH:7][n:8][cH:9][cH:10]1Participants
11
Reactant 10
HCID 175Acetate2×
HCID 313Hydrochloric Acid2×
HCID 923Sodium ion2×
HCID 3776Isopropanol
HCID 11776Triphenylphosphine
HCID 19660Carbonate Ion
HCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)
HCID 27625564-Methoxypyridine-3-boronic acid
HCID 597442655-(4-Bromobenzyl)-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinoline-6-carboxylic acid tert-butyl ester
HCID 690813245-[[4-(4-Methoxy-3-pyridinyl)phenyl]methyl]-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolineProduct 1
Sources & evidence
- ORD record
- ord-56b98acab276464b86c53f156fcedb15
- Source dataset
- Training data from https://doi.org/10.1039/C8SC04228D (1/10)
Reaction notes
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