Tetrahydrofuran → 1-[5-Chloro-8-(3-fluorophenyl)isoquinolin-7-yl]ethanol

HRID 1192592Notes

Reaction equation

HRID 1192592 reaction equation
[Cl-].[NH4+:2].C([O-])(=O)C.[Na+].[Cl:8][C:9]1[C:10]([CH2:27][CH:28]=O)=[C:11]([CH:25]=O)[C:12]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)=[C:13]([CH:15]([OH:17])[CH3:16])[CH:14]=1.O1CCCC1>O>[Cl:8][C:9]1[CH:14]=[C:13]([CH:15]([OH:17])[CH3:16])[C:12]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)=[C:11]2[C:10]=1[CH:27]=[CH:28][N:2]=[CH:25]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 517045Sodium AcetateHCID 583686864-Chloro-3'-fluoro-6-(1-hydroxyethyl)-3-(2-oxoethyl)biphenyl-2-carbaldehyde

Product 1

HCID 583686851-[5-Chloro-8-(3-fluorophenyl)isoquinolin-7-yl]ethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ammonium chloride (28.5 mg, 0.533 mmol) and sodium acetate (43.7 mg, 0.533 mmol) in water (0.4 mL) was added to a solution of 4-chloro-3′-fluoro-6-(1-hydroxyethyl)-3-(2-oxoethyl)biphenyl-2-carbaldehyde (0.171 g, 0.533 mmol) in tetrahydrofuran (0.4 mL, 5 mmol). The reaction mixture was stirred at room temperature overnight and then extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate, concentrated to dryness under reduced pressure. The crude product was used in the next step (0.16 g, 99%). LCMS calculated for C17H14ClFNO (M+H)+: m/z=302.1; Found: 302.1

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-bbd83490899544a0aafc6636aac60698
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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