Sodium Hydroxide → HCID 86710449, compound

HRID 2168845Notes

Reaction equation

HRID 2168845 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:7]=[CH:8][C:9]([O:25]C)=[C:10]([N:12]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:11]=1.C(=O)(O)[O-].[Na+].[OH-].[Na+]>ClCCl>[CH:23]1[C:24]2[N:12]([C:10]3[CH:11]=[C:6]([F:5])[CH:7]=[CH:8][C:9]=3[OH:25])[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:19]=2[CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 86710448HCID 86710448, compound

Product 1

HCID 86710449HCID 86710449, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A 1.0 M boron tribromide solution in dichloro-methane (60 mL, 60 mmol, 3 equiv) was added dropwise over 30 minutes at −78° C. to a solution of compound 4 (5.8 g, 20 mmol, 1 equiv) in dichloromethane (60 mL). The reaction was stirred at −78° C. for 4 hours, when 1H-NMR indicated that the reaction was complete. The reaction was poured into saturated sodium bicarbonate (100 mL) and the pH adjusted to 8 with 10% sodium hydroxide. The layers were separated and the aqueous phase was extracted with dichloro-methane (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified over silica gel (100 g), eluting with a gradient of 60 to 100% dichloromethane in heptanes. The product containing fractions were combined, concentrated under reduced pressure and triturated with 20% methyl tert-butyl ether in heptanes (10 mL) to give compound 5 (4.3 g, 78% yield) as a white solid.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with dichloro-methane (3×20 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified over silica gel (100 g)
  7. washeluting with a gradient of 60 to 100% dichloromethane in heptanes
  8. additionThe product containing fractions
  9. concentrationconcentrated under reduced pressure
  10. customtriturated with 20% methyl tert-butyl ether in heptanes (10 mL)

Sources & evidence

ORD record
ord-c427e2696b98432e95624e31cf6464e5
Source dataset
uspto-grants-2015_06
Patent number
US09045568B2

Reaction notes

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