Diisobutylaluminumhydride → HCID 86709317, compound

HRID 529405Notes

Reaction equation

HRID 529405 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([CH2:24][C:25](OC(C)(C)C)=[O:26])[NH:17][S:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19].[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[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([NH:17][S:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])[CH2:24][CH2:25][OH:26]

Participants

4

Reactant 2

HCID 21225700Diisobutylaluminumhydride2×HCID 86709318HCID 86709318, compound

Product 1

HCID 86709317HCID 86709317, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 2-(7-bromo-3-chloro-5-(1,1-dimethylethylsulfinamido)-5H-chromeno[2,3-c]pyridin-5-yl)acetate (isomer A) (720 mg, 1.359 mmol) in dry THF (5.5 mL) was brought to −78° C. and diisobutylaluminum hydride (5.44 mL, 5.44 mmol) was added slowly. The mixture was brought to 0° C. after diisobutylaluminum hydride addition, and stirred at this temperature for 0.5 hr. The reaction mixture was quenched with saturated Rochelle's salt (˜40 mL) and stirred at RT for overnight. The organic layer was separated and the aqueous phase was extracted by EtOAc. The combined organics were washed with saturated NaCl aqueous solution, dried over MgSO4, filtered, and concentrated to afford N-(7-bromo-3-chloro-5-(2-hydroxyethyl)-5H-chromeno[2,3-c]pyridin-5-yl)-2-methylpropane-2-sulfinamide as off-white solid that was advanced without further purification.

Workup

  1. customwas brought to −78° C.
  2. customwas brought to 0° C.
  3. customThe reaction mixture was quenched with saturated Rochelle's salt (˜40 mL)
  4. stirringstirred at RT for overnight
  5. customThe organic layer was separated
  6. extractionthe aqueous phase was extracted by EtOAc
  7. washThe combined organics were washed with saturated NaCl aqueous solution
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-12c39bf42c054e4b8fdb2f86dc4c665a
Source dataset
uspto-grants-2016_05
Patent number
US09346827B2

Reaction notes

Loading…