Hydrochloric Acid → HCID 39231616, compound

HRID 1500496Notes

Reaction equation

HRID 1500496 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([F:15])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1)#[N:2].B.Cl.[OH-].[Na+]>O1CCCC1>[F:15][C:6]1[CH:5]=[CH:4][C:3]([CH2:1][NH2:2])=[CH:8][C:7]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 14798Sodium HydroxideHCID 46314741HCID 46314741, compound

Product 1

HCID 39231616HCID 39231616, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-cyano-2-fluorobiphenyl (1.96 g) in tetrahydrofuran (35 mL), a solution of borane in tetrahydrofuran (1 M, 35 mL) was added dropwise at room temperature, and the mixture was stirred for 22 hours. Hydrochloric acid (1 M, 7 mL) was gradually added dropwise to the reaction solution, and the mixture was stirred for 2 hours. A 2 M aqueous sodium hydroxide solution was added thereto for separation into organic and aqueous layers. The aqueous layer was subjected to extraction with ethyl acetate. All the organic layers were combined, dried over anhydrous sodium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column (Biotage Ltd., elution solvent: hexane/ethyl acetate) to obtain the title compound (1.25 g).

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. customfor separation into organic and aqueous layers
  3. extractionThe aqueous layer was subjected to extraction with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by chromatography on a silica gel column (Biotage Ltd., elution solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3ba5773ad8c443199cdc6da7595911db
Source dataset
uspto-grants-2015_12
Patent number
US09206168B2

Reaction notes

Loading…