3-Pyridinylboronic acid → HCID 68227449, compound

HRID 1037424Notes

Reaction equation

HRID 1037424 reaction equation
Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11](=[O:12])[C:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]4([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:21][CH2:20]4)=[CH:15][CH:14]=3)=[C:9]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:8][C:7]=12.[N:37]1[CH:42]=[CH:41][CH:40]=[C:39](B(O)O)[CH:38]=1>>[O:12]=[C:11]1[C:6]2[C:7](=[C:2]([C:39]3[CH:38]=[N:37][CH:42]=[CH:41][CH:40]=3)[N:3]=[CH:4][CH:5]=2)[O:8][C:9]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[C:10]1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 86671031tert-Butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate

Product 1

HCID 68227449HCID 68227449, compoundYield 37%

Procedure

Following the procedure used to prepare tert-butyl 1-(4-(8-(1-isobutyl-1H-pyrazol-4-yl)-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutyl carbamate, tert-butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate was reacted with pyridine-3-boronic acid to give the title compound (20 mg, 37%). LCMS (Method I): RT=7.45 min, [M+H]+=546.

Sources & evidence

ORD record
ord-cfb9877f0a9b4a0cbab0a5445b4aecd6
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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