Citric Acid → 2-tert-butoxycarbonylamino-5-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzoic acid

HRID 817939Notes

Reaction equation

HRID 817939 reaction equation
[Br:35][c:36]1[cH:37][cH:38][c:39]([NH:45][C:46](=[O:47])[O:48][C:49]([CH3:50])([CH3:51])[CH3:52])[c:40]([C:41](=[O:42])[OH:43])[cH:44]1.[C:53](=[O:54])([OH:55])[O-:56].[CH3:1][O:2][c:3]1[c:4](-[c:9]2[n:10][n:11]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:33])[CH3:34])[c:12]3[n:13][cH:14][c:15]([B:18]4[O:19][C:20]([CH3:21])([CH3:22])[C:23]([CH3:24])([CH3:25])[O:26]4)[cH:16][c:17]23)[cH:5][cH:6][cH:7][cH:8]1.[CH3:71][CH2:72][O:73][C:74](=[O:75])[CH3:76].[CH3:77][C:78]#[N:79].[Na+:57].[OH:58][C:59]([CH2:60][C:61]([C:62](=[O:63])[OH:64])([CH2:65][C:66](=[O:67])[OH:68])[OH:69])=[O:70]>>[CH3:1][O:2][c:3]1[c:4](-[c:9]2[n:10][n:11]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:33])[CH3:34])[c:12]3[n:13][cH:14][c:15](-[c:36]4[cH:37][cH:38][c:39]([NH:45][C:46](=[O:47])[O:48][C:49]([CH3:50])([CH3:51])[CH3:52])[c:40]([C:41](=[O:42])[OH:43])[cH:44]4)[cH:16][c:17]23)[cH:5][cH:6][cH:7][cH:8]1

Participants

8

Reactant 7

HCID 311Citric AcidHCID 769Bicarbonate IonHCID 923Sodium ionHCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 723356N-Boc-5-Bromoanthranilic acidHCID 598360923-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxy-methyl)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 579759012-tert-butoxycarbonylamino-5-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-benzoic acid

Sources & evidence

ORD record
ord-05e8f72d15ed48639e015adc156bde26
Source dataset
Test data from https://doi.org/10.1039/C8SC04228D

Reaction notes

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