Potassium Carbonate → HCID 86587382, compound

HRID 1357245Notes

Reaction equation

HRID 1357245 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]([OH:21])=[CH:19][CH:18]=[C:17]3[C:12]=2[CH:13]=[CH:14][C:15]([CH2:22][NH:23][C:24]([C:26]2[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[O:28][C:27]=2[CH2:35][CH2:36][CH2:37][CH3:38])=[O:25])=[CH:16]3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:40][C:41]#[N:42].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:20]([O:21][CH2:40][C:41]#[N:42])=[CH:19][CH:18]=[C:17]3[C:12]=2[CH:13]=[CH:14][C:15]([CH2:22][NH:23][C:24]([C:26]2[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=4[O:28][C:27]=2[CH2:35][CH2:36][CH2:37][CH3:38])=[O:25])=[CH:16]3)=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 86587383HCID 86587383, compound

Product 1

HCID 86587382HCID 86587382, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-butyl-benzofuran-3-carboxylic acid [5-(4-tert-butyl-phenyl)-6-hydroxy-naphthalen-2-ylmethyl]-amide (400 mg, 0.79 mmol), prepared in the previous step, bromoacetonitrile (66 μL, 0.95 mmol) and potassium carbonate (547 mg, 3.96 mmol) in 20 mL of DMF was stirred under nitrogen at room temperature for 19 h (overnight). The reaction was diluted with ethyl acetate, extracted multiple times with water, dried (MgSO4) and the solvent removed under reduced pressure to give a light brown solid. Purification of the solid on a 40 g KP-SIL 60 Δ Biotage column gave 2-butyl-benzofuran-3-carboxylic acid [5-(4-tert-butyl-phenyl)-6-cyanomethoxy-naphthalen-2-ylmethyl]-amide (262 mg, 63%) as a white solid, mp 162-164° C.

Workup

  1. extractionextracted multiple times with water
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure
  4. customto give a light brown solid
  5. customPurification of the solid on a 40 g KP-SIL 60 Δ Biotage column

Sources & evidence

ORD record
ord-a950dc1573ce45d6a577b1311757a593
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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