{1-[4-(6-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester → tert-Butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate

HRID 1037259Notes

Reaction equation

HRID 1037259 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15](C3C(=O)C4C(=CC=C(F)C=4)OC=3C3C=CC=CC=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl:37][C:38]1[N:39]=[CH:40][CH:41]=[C:42]2[C:47](=[O:48])[C:46](I)=[C:45]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[O:44][C:43]=12>>[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:46]3[C:47](=[O:48])[C:42]4[C:43]([O:44][C:45]=3[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[C:38]([Cl:37])[N:39]=[CH:40][CH:41]=4)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 67067635{1-[4-(6-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterHCID 86671032HCID 86671032, compound

Product 1

HCID 86671031tert-Butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamateYield 20%

Procedure

Following the procedure used to prepare {1-[4-(6-fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester, 8-chloro-3-iodo-2-phenyl-pyrano[2,3-c]pyridin-4-one was reacted to give the title compound (30 mg, 20%) as a white solid. LCMS (Method A): RT=4.88 min, [M+Na]+=525/527.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-4ab718eac1c144ebab954573588b06af
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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