1,2-Dichloroethane → HCID 90408338, compound

HRID 594025Notes

Reaction equation

HRID 594025 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([B:8]([OH:10])[OH:9])[CH:7]=1.[C:12]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][N:24]=1)[C:19]([OH:21])=O)([CH3:15])([CH3:14])[CH3:13].[CH2:25](Cl)[CH2:26]Cl.ON1[C:34]2N=CC=[CH:38][C:33]=2N=N1.[CH3:39]N(C=O)C>CCOC(C)=O.O>[C:12]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][N:24]=1)[C:19]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([B:8]2[O:10][C:33]([CH3:38])([CH3:34])[C:25]([CH3:26])([CH3:39])[O:9]2)[CH:7]=1)=[O:21])([CH3:13])([CH3:14])[CH3:15]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 181649HOAtHCID 6932922-(tert-Butyl)isonicotinic acidHCID 57497242HCID 57497242, compound

Product 1

HCID 90408338HCID 90408338, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-amino-2-methylphenylboronic acid, pinacol ester (1.0 equiv.), 2-(tert-butyl)isonicotinic acid (1.0 equiv.), EDC (1.0 equiv.) and 1-hydroxy-7-azabenzotriazole (0.380 g, 1.0 equiv.) in DMF (0.3 M) was stirred at RT for 68 hr. The reaction mixture was then diluted with EtOAc and water, the organic layer was isolated and the aqueous layer was extracted twice with EtOAc. The combined organics were dried over MgSO4, filtered and concentrated in vaccuo to yield 2-(tert-butyl)-N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)isonicotinamide as a white solid in 91%. LCMS (m/z) (M+H)=395.1, Rt=0.71 min.

Workup

  1. customthe organic layer was isolated
  2. extractionthe aqueous layer was extracted twice with EtOAc
  3. dry with materialThe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vaccuo

Sources & evidence

ORD record
ord-99309c1b4ff347b181218128b771f694
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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