HCID 57443610, compound → HCID 86610107, compound

HRID 1157415Notes

Reaction equation

HRID 1157415 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[CH:16]=[C:15]([C:17]#[CH:18])[CH:14]=[CH:13][C:12]=2[Cl:19])[CH:9]=1)[C:5]#[N:6].I[C:21]1[C:29]2[C:24](=NC=CC=2)[N:23]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[N:22]=1>CN(C=O)C.C1(P([Pd-](Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[C:33]([O:32][C:30]([N:23]1[C:24]2[CH:3]=[CH:4][CH:5]=[N:6][C:29]=2[C:21]([C:18]#[C:17][C:15]2[CH:14]=[CH:13][C:12]([Cl:19])=[C:11]([O:10][C:8]3[CH:7]=[C:4]([C:5]#[N:6])[CH:3]=[C:2]([Cl:1])[CH:9]=3)[CH:16]=2)=[N:22]1)=[O:31])([CH3:34])([CH3:35])[CH3:36]

Participants

6

Reactant 2

HCID 57443610HCID 57443610, compoundHCID 574436133-Chloro-5-(2-chloro-5-ethynylphenoxy)benzonitrile

Product 1

HCID 86610107HCID 86610107, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178479804HCID 178479804, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 147 mg (0.51 mmol) of 3-chloro-5-(2-chloro-5-ethynylphenoxy)benzonitrile, 166 mg (0.48 mmol) of tert-butyl 3-iodo-1H-pyrazolo[3,4-b]pyridine-1-carboxylate, 17 mg (0.03 mmol) of bis(triphenylphosphino)palladium (II) chloride, and 9.00 mg (0.05 mmol) of CuI in 2.5 mL DMF/5 mL triethylamine under nitrogen was stirred at room temperature for one hour. The reaction mixture was concentrated in vacuo to a dark oil. The crude oil was purified by flash chromatography over silica gel with 2.5:1 hexanes/EtOAc to provide the desired product as a yellow oil/foam. M+=405 (M−100, loss of Boc). 1H NMR (CDCl3): 1.75 (s, 9H), 7.10 (m, 1H), 7.19 (m, 1H), 7.36 (m, 1H), 7.39 (m, 2H), 7.50 (dd, 1H), 7.56 (dd, 1H), 8.21 (dd, 1H), 8.82 (dd, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to a dark oil
  2. customThe crude oil was purified by flash chromatography over silica gel with 2.5:1 hexanes/EtOAc

Sources & evidence

ORD record
ord-5ca82305dec94a28bf5c6f8971e1be4f
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

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