7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-one → tert-butyl 2-(7-bromo-3-chloro-1-fluoro-5-hydroxy-5H-chromeno[2,3-c]pyridin-5-yl)acetate

HRID 455584Notes

Reaction equation

[Cl-].[C:2]([O:6][C:7](=[O:10])[CH2:8][Zn+])([CH3:5])([CH3:4])[CH3:3].[Br:11][C:12]1[CH:13]=[C:14]2[C:25](=[CH:26][CH:27]=1)[O:24][C:17]1[C:18]([F:23])=[N:19][C:20]([Cl:22])=[CH:21][C:16]=1[C:15]2=[O:28]>C1COCC1>[Br:11][C:12]1[CH:13]=[C:14]2[C:25](=[CH:26][CH:27]=1)[O:24][C:17]1[C:18]([F:23])=[N:19][C:20]([Cl:22])=[CH:21][C:16]=1[C:15]2([CH2:8][C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:10])[OH:28]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2-tert-butoxy-2-oxoethyl)zinc(II) chloride (0.5M in Et2O; 670 ml, 335 mmol) at 0° C. was added drop wise a solution of 7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-one (55 g, 167 mmol) in THF (30 mL). The resulting reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was quenched with aqueous, saturated NH4Cl solution and extracted with EtOAc. The organic extracts were dried over Na2SO4 and concentrated under reduced pressure to afford tert-butyl 2-(7-bromo-3-chloro-1-fluoro-5-hydroxy-5H-chromeno[2,3-c]pyridin-5-yl)acetate (66.0 g, 148 mmol, 89% yield) as a yellow solid.

Workup

customThe resulting reaction mixture
customThe reaction mixture was quenched with aqueous, saturated NH4Cl solution
extractionextracted with EtOAc
dry with materialThe organic extracts were dried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-4e792dbb382b45a38801417c412482d2
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497264B2

Reaction notes

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