Benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzoate → 3-{4-[(benzyloxy)carbonyl]phenyl}-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 575002Notes

Reaction equation

HRID 575002 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:24]=[CH:23][C:12]([C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])=[CH:11][CH:10]=2)O1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:34]=[C:35]([C:49]([OH:51])=[O:50])[C:36]3[C:41](I)=[N:40][N:39]([CH:43]4[CH2:48][CH2:47][CH2:46][CH2:45][O:44]4)[C:37]=3[N:38]=2)=[CH:29][C:28]=1[C:52]([O:54][CH3:55])=[O:53]>>[CH2:16]([O:15][C:13]([C:12]1[CH:11]=[CH:10][C:9]([C:41]2[C:36]3[C:35]([C:49]([OH:51])=[O:50])=[CH:34][C:33]([C:30]4[CH:31]=[CH:32][C:27]([F:26])=[C:28]([C:52]([O:54][CH3:55])=[O:53])[CH:29]=4)=[N:38][C:37]=3[N:39]([CH:43]3[CH2:48][CH2:47][CH2:46][CH2:45][O:44]3)[N:40]=2)=[CH:24][CH:23]=1)=[O:14])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 72208524Benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)benzoateHCID 1177781086-[4-fluoro-3-(methoxycarbonyl)phenyl]-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Product 1

HCID 1177779833-{4-[(benzyloxy)carbonyl]phenyl}-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidYield 66%

Procedure

Obtained according to the process described in Step 3.1, using benzyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate and 6-[4-fluoro-3-(methoxycarbonyl)phenyl]-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid [described in Step 1.7], in the form of a yellow solid (yield: 66%).

Workup

  1. customObtained

Sources & evidence

ORD record
ord-926114ead8cf46f68e3afee4819c8fd2
Source dataset
uspto-grants-2015_05
Patent number
US09034898B2

Reaction notes

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