Dimethylformamide → 4-[7-(3-Imidazol-1-ylprop-1-ynyl)-3-oxo-2H-isoquinolin-2-ylmethyl]benzoic Acid tert-butyl Ester

HRID 488786Notes

Reaction equation

HRID 488786 reaction equation
[C:1]([O:5][C:6](=[O:26])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:23](=[O:24])[CH:22]=[C:21]3[C:16]([CH:17]=[C:18](Br)[CH:19]=[CH:20]3)=[CH:15]2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C([CH:30]1C=NN=[N:31]1)C#C.[CH2:35](N(CC)CC)[CH3:36].[CH3:42][N:43]([CH3:46])[CH:44]=O>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6](=[O:26])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:23](=[O:24])[CH:22]=[C:21]3[C:16]([CH:17]=[C:18]([C:35]#[C:36][CH2:42][N:43]4[CH:46]=[CH:30][N:31]=[CH:44]4)[CH:19]=[CH:20]3)=[CH:15]2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 222653234-prop-2-ynyl-4H-triazoleHCID 865911974-(7-bromo-3-oxo-2H-isoquinolin-2-ylmethyl)benzoic acid tert-butyl ester

Product 1

HCID 104783554-[7-(3-Imidazol-1-ylprop-1-ynyl)-3-oxo-2H-isoquinolin-2-ylmethyl]benzoic Acid tert-butyl Ester

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

The coupling of 4-(7-bromo-3-oxo-2H-isoquinolin-2-ylmethyl)benzoic acid tert-butyl ester (0.80 g, 1.93 mmol) with 4-prop-2-ynyl-4H-triazole (0.41 g, 3.86 mmol) using triethylamine (1.08 mL, 7.22 mmol), CuI (0.026 g, 0.14 mmol), and Pd(Ph3P)4 (0.15 g, 0.13 mmol) in dimethyl-formamide is carried out as described in Example 1, Step (2). Purification on a silica gel column eluted with hexane/ethyl acetate 2:1, ethyl acetate, and methylene chloride/THF 4:1, followed by drying, will afford the desired product.

Workup

  1. customPurification on a silica gel column
  2. washeluted with hexane/ethyl acetate 2:1, ethyl acetate, and methylene chloride/THF 4:1
  3. customby drying

Sources & evidence

ORD record
ord-2845b3bd2a85482a837d079567afcfe3
Source dataset
uspto-grants-2005_12
Patent number
US06974822B2

Reaction notes

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