3-Fluoro-5-hydroxybenzeneboronic acid → tert-butyl 3-(4-(3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)-1,2,3,6-tetrahydropyridine-1-carbonyl)azetidine-1-carboxylate

HRID 634502Notes

Reaction equation

HRID 634502 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[O:15][C:16](=[O:43])[C:17]4[C:22]([C:23]=3[C:24]3[CH2:25][CH2:26][N:27]([C:30]([CH:32]5[CH2:35][N:34]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:33]5)=[O:31])[CH2:28][CH:29]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH3:13])[N:9]=[C:10](I)[C:3]=12.[F:44][C:45]1[CH:46]=[C:47](B(O)O)[CH:48]=[C:49]([OH:51])[CH:50]=1>>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]([C:14]3[O:15][C:16](=[O:43])[C:17]4[C:22]([C:23]=3[C:24]3[CH2:25][CH2:26][N:27]([C:30]([CH:32]5[CH2:35][N:34]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:33]5)=[O:31])[CH2:28][CH:29]=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH3:13])[N:9]=[C:10]([C:47]3[CH:48]=[C:49]([OH:51])[CH:50]=[C:45]([F:44])[CH:46]=3)[C:3]=12

Participants

3

Reactant 2

HCID 447173083-Fluoro-5-hydroxybenzeneboronic acidHCID 118131140tert-butyl 3-(4-(3-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)-1,2,3,6-tetrahydropyridine-1-carbonyl)azetidine-1-carboxylate2×

Product 1

HCID 118131360tert-butyl 3-(4-(3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)-1,2,3,6-tetrahydropyridine-1-carbonyl)azetidine-1-carboxylateYield 63.2%

Procedure

The title compound was prepared following the procedure reported for Example 68, from tert-butyl 3-(4-(3-(1-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)-1,2,3,6-tetrahydropyridine-1-carbonyl)azetidine-1-carboxylate (Intermediate D28, 0.251 g, 0.360 mmol), and 3-fluoro-5-hydroxyphenylboronic acid (0.112 g, 0.720 mmol) to give tert-butyl 3-(4-(3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)-1,2,3,6-tetrahydropyridine-1-carbonyl)azetidine-1-carboxylate (0.155 g, 0.227 mmol, 63.2% yield).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-6f2ca7e4560f498da9792dce8a0749d2
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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