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(NZ)-N-(7-bromo-3-chloro-1-fluorochromeno[2,3-c]pyridin-5-ylidene)-2-methylpropane-2-sulfinamide → tert-butyl 2-(7-bromo-3-chloro-5-(1,1-dimethylethylsulfinamido)-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)acetate

HRID 455577
Notes
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Reaction equation

HRID 455577 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=[N:28]\[S:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30]>C1COCC1.CCOC(C)=O>[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])[NH:28][S:29]([C:31]([CH3:34])([CH3:33])[CH3:32])=[O:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 87400620(NZ)-N-(7-bromo-3-chloro-1-fluorochromeno[2,3-c]pyridin-5-ylidene)-2-methylpropane-2-sulfinamideHCID 178451183HCID 178451183, compound

Product 1

HCID 86658360tert-butyl 2-(7-bromo-3-chloro-5-(1,1-dimethylethylsulfinamido)-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)acetateYield 59.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
0 °C

Procedure

A solution of (2-tert-butoxy-2-oxoethyl)zinc (II) chloride (0.5M in Et2O; 116 mL, 57.9 mmol) was cooled to 0° C. and a solution of (Z)—N-(7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-ylidene)-2-methylpropane-2-sulfinamide (10 g, 23.16 mmol) in THF (100 mL) was added drop wise. The resulting mixture was stirred at for 1 hour 0° C. The reaction mixture was diluted with EtOAc and washed with aqueous saturated solution of NH4Cl, followed by brine. The organic layer was dried over Na2SO4, and concentrated under reduced pressure. The obtained residue was purified by chromatography (0-20% EtOAc/hexanes) to afford tert-butyl 2-(7-bromo-3-chloro-5-(1,1-dimethylethylsulfinamido)-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)acetate (7.5 g, 13.69 mmol, 59.1% yield) as a yellow solid.

Workup

  1. washwashed with aqueous saturated solution of NH4Cl
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by chromatography (0-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-bd5ebb5e0344448e85a49adb887185af
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08497264B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes