Sodium Chloride → HCID 57656114, compound

HRID 2041146Notes

Reaction equation

HRID 2041146 reaction equation
FC(F)(F)C([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)=O.Br[C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[C:20]#[N:21].[OH-].[Na+].[Cl-].[Na+]>CO.C(Cl)Cl>[NH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:17]2[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=2)[C:20]#[N:21])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 233813-BromobenzonitrileHCID 57656322HCID 57656322, compound

Product 1

HCID 57656114HCID 57656114, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Use a method similar to Preparation 40 (Step 2), using 2,2,2-trifluoro-N-(4-hydroxybenzyl)-acetamide (1.0 g, 5.5 mmol) and 3-bromobenzonitrile (673 mg, 3.7 mmol). Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 3:1). Concentrate in vacuo. Dissolve the residue (287 mg, 0.89 mmol) in methanol (25 mL) and add 5N NaOH (7 mL). Stir at room temperature for 4 h. Dilute with DCM and add solid sodium chloride to the mixture. Extract the aqueous layer three times with DCM. Combine organic extracts, dry over Na2SO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with DCM/2M ammonia in methanol (94:6) to obtain the title compound (124 mg, 62%). MS (ES+) m/z: 500 (M+H)+.

Workup

  1. customsimilar to Preparation 40 (Step 2)
  2. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0 and 3:1)
  3. concentrationConcentrate in vacuo
  4. extractionExtract the aqueous layer three times with DCM
  5. dry with materialCombine organic extracts, dry over Na2SO4
  6. concentrationconcentrate in vacuo
  7. customPurify by chromatography on silica gel eluting with DCM/2M ammonia in methanol (94:6)

Sources & evidence

ORD record
ord-855e19ee010b49a888fbcd1a2076e684
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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