Sodium Bicarbonate → (NE,R)-N-(7-bromo-3-chlorochromeno[2,3-c]pyridin-5-ylidene)-2-methylpropane-2-sulfinamide

HRID 529403

Reaction equation

HRID 529403 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1[CH:8]=[N:9][C:10]([Cl:12])=[CH:11][C:6]=1[C:5]2=O.[CH3:18][C:19]([S@:22]([NH2:24])=[O:23])([CH3:21])[CH3:20].C(=O)(O)[O-].[Na+]>C1COCC1.[Cl-].[Na+].O.C(O[Ti](OCC)(OCC)OCC)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1[CH:8]=[N:9][C:10]([Cl:12])=[CH:11][C:6]=1/[C:5]/2=[N:24]/[S@@:22]([C:19]([CH3:21])([CH3:20])[CH3:18])=[O:23]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 574756367-Bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-one

Product 1

HCID 88920351(NE,R)-N-(7-bromo-3-chlorochromeno[2,3-c]pyridin-5-ylidene)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 3

HCID 178477244HCID 178477244, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-one (5.0 g, 48.3 mmol), (R)-2-methylpropane-2-sulfinamide (5.85 g, 48.3 mmol), and tetraethoxytitanium (10.00 mL, 48.3 mmol) in dry THF (100 mL) was heated at 75° C. for 24 hours. The solution was cooled to RT and slowly poured into a 2 L flask containing 0.35 L of brine and 0.35 L of saturated sodium bicarbonate. The resulting mixture was stirred vigorously for 15 minutes before being filtered through a pad of celite. The pad was washed with EtOAc. The filtrate was poured into a separatory funnel and the aqueous layer was extracted with EtOAc (2×500 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to provide an orange solid. This solid was purified by silica gel chromatography using 0-15% Hexane/EtOAC to provide (R,E)-N-(7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-ylidene)-2-methylpropane-2-sulfinamide as an orange solid. [email protected] min.

Workup

  1. temperatureThe solution was cooled to RT
  2. additionslowly poured into a 2 L flask
  3. filtrationbefore being filtered through a pad of celite
  4. washThe pad was washed with EtOAc
  5. additionThe filtrate was poured into a separatory funnel
  6. extractionthe aqueous layer was extracted with EtOAc (2×500 mL)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto provide an orange solid
  12. customThis solid was purified by silica gel chromatography

Sources & evidence

ORD record
ord-43158cf967ec4d629694d9226d79841b
Source dataset
uspto-grants-2016_05
Patent number
US09346827B2

Linked notes

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