Dimethylformamide → HCID 68183793, compound

HRID 2199988Notes

Reaction equation

HRID 2199988 reaction equation
Cl[C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:12]=2)[C:7]([CH3:19])=[N:6]1.C1(P(C2CCCCC2)C2(C(C)C)CC(C(C)C)=CC(C(C)C)=C2C2C=CC=CC=2)CCCCC1.[CH3:59][N:60](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:2]([C:59]#[N:60])[C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:12]=2)[C:7]([CH3:19])=[N:6]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 575232193-[1-(2,6-dichlorobenzyl)-3-methyl-1H-indazole-6-yl]propionic acidHCID 672859322-Dicyclohexylphosphino-2,4,6-triisopropylbiphenyl

Product 1

HCID 68183793HCID 68183793, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

To a solution of the compound [122] (29.7 mg) in N,N-dimethylformamide (0.8 mL) were added zinc cyanide (4.8 mg), tris(dibenzylideneacetone)dipalladium(0) (3.7 mg) and 2-dicyclohexylphosphino-2,4,6-triisopropylbiphenyl (7.8 mg) at room temperature, and then the reaction mixture was subjected to microwave irradiation at 160° C. for 30 minutes. The reaction mixture was quenched with water, and extracted with ethyl acetate, and then the obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by reverse phase preparative liquid chromatography to give the titled compound (13.3 mg) as a white solid.

Workup

  1. customirradiation at 160° C. for 30 minutes
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialthe obtained organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by reverse phase preparative liquid chromatography

Sources & evidence

ORD record
ord-41d2fffc788f41cb8716f34bacb75b7f
Source dataset
uspto-grants-2016_06
Patent number
US09359350B2

Reaction notes

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