Sodium Chloride → HCID 57656114, compound

HRID 911259Notes

Reaction equation

HRID 911259 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-92d5e00802284d959229038fbb12ee5f
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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