Triethylamine → HCID 22268228, compound

HRID 488784Notes

Reaction equation

HRID 488784 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([F:20])[CH:14]=1)[C:7](=[O:21])[CH:6]=2.[C:22]1([CH2:28][C:29]#[CH:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>CN(C)C=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>[F:20][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][C:16]=1[F:19])[CH2:12][N:8]1[C:7](=[O:21])[CH:6]=[C:5]2[C:10]([N:11]=[C:2]([C:30]#[C:29][CH2:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:3]=[N:4]2)=[CH:9]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 575753BenzylacetyleneHCID 22268260HCID 22268260, compound

Product 1

HCID 22268228HCID 22268228, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

The coupling of 7-bromo-2-(3,4-difluorobenzyl)-2H-5,8-diazaisoquinolin-3-one (0.80 g, 2.28 mmol) with 3-phenyl-1-propyne (0.71 mL, 5.74 mmol) using triethylamine (0.64 mL, 4.59 mmol), CuI (0.031 g, 0.16 mmol), and Pd(Ph3P)4 (0.106 g, 0.092 mmol) in dimethylformamide (6 mL) is carried out as described in Example 1, Step (2). The resulting red oil is evaporated onto silica gel and purified on a 3.5×20 cm silica gel column eluted with hexanes/ethyl acetate 3:1. The resulting red solid is triturated with ethyl ether and dried. This will afford the desired product.

Workup

  1. customThe resulting red oil is evaporated onto silica gel
  2. custompurified on a 3.5×20 cm silica gel column
  3. washeluted with hexanes/ethyl acetate 3:1
  4. customThe resulting red solid is triturated with ethyl ether
  5. customdried

Sources & evidence

ORD record
ord-8500de721da64b0983e9cd628526297b
Source dataset
uspto-grants-2005_12
Patent number
US06974822B2

Reaction notes

Loading…