Sodium borohydride → HCID 68817418, compound

HRID 734731Notes

Reaction equation

HRID 734731 reaction equation
[NH2:1][S:2]([C:5]1[C:6]([Cl:16])=[CH:7][C:8]([F:15])=[C:9]([CH:14]=1)[C:10](OC)=[O:11])(=[O:4])=[O:3].[Cl-].[Cl-].[Ca+2].[BH4-].[Na+]>C1COCC1.CCO>[Cl:16][C:6]1[CH:7]=[C:8]([F:15])[C:9]([CH2:10][OH:11])=[CH:14][C:5]=1[S:2]([NH2:1])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 13318612HCID 13318612, compound

Product 1

HCID 68817418HCID 68817418, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of methyl 5-(aminosulfonyl)-4-chloro-2-fluorobenzoate (500 mg, 1.87 mmol) in THF/EtOH (20 mL, 1:1), CaCl2 (415 mg, 3.74 mmol) and NaBH4 (283 mg, 7.48 mmol) were added in one portion respectively. The reaction mixture was stirred at room temperature for 6 hours, quenched with water. 1 M aqueous citric acid (5 mL) was added to the mixture and extracted with EtOAc (3×100 mL). The extracts were combined, washed with brine, and dried (Na2SO4). The solvent was evaporated to afford the product (440 mg, 98%) as a white solid. MS (ES+) m/z 262 [M+Na]+.

Workup

  1. customquenched with water
  2. addition1 M aqueous citric acid (5 mL) was added to the mixture
  3. extractionextracted with EtOAc (3×100 mL)
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4168e7733e054e34a3185a99248919ab
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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