{1-[4-(6-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester → {1-[4-(7-Chloro-4-oxo-2-phenyl-4H-pyrano[2,3-b]pyridin-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

HRID 1037248Notes

Reaction equation

HRID 1037248 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:43]=[C:42]2[O:44][C:45]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[C:46](I)[C:47](=[O:48])[C:41]2=[CH:40][CH:39]=1>>[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:41]4[C:42]([O:44][C:45]=3[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[N:43][C:38]([Cl:37])=[CH:39][CH:40]=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 866710247-Chloro-3-iodo-2-phenyl-pyrano[2,3-b]pyridin-4-one

Product 1

HCID 86671025{1-[4-(7-Chloro-4-oxo-2-phenyl-4H-pyrano[2,3-b]pyridin-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterYield 64%

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, 7-chloro-3-iodo-2-phenyl-pyrano[2,3-b]pyridin-4-one was reacted to give the title compound (8.4 mg, 64%) as a colourless gum. LCMS (Method B): RT=4.42 min, [M+Na]+=525/527.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-1dfcaed8ac9b406eb72941e59857e441
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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