tert-Butyl (5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate → 2-((2,4-Dimethylphenyl)ethynyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine
Reaction equation
Cl[C:2]1[C:3]([C:18]#[N:19])=[N:4][CH:5]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=2[CH3:17])[CH:7]=1.[CH3:20][C:21]1[CH:22]=[CH:23][C:24](B2OC(C)(C)C(C)(C)O2)=[C:25]([NH:27]C(=O)OC(C)(C)C)[CH:26]=1>>[CH3:17][C:11]1[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:10]=1[C:9]#[C:8][C:6]1[CH:5]=[N:4][C:3]2[C:2]([CH:7]=1)=[C:24]1[CH:23]=[CH:22][C:21]([CH3:20])=[CH:26][C:25]1=[N:27][C:18]=2[NH2:19]Participants
3
Procedure
2-((2,4-Dimethylphenyl)ethynyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine was prepared from 3-chloro-5-((2,4-dimethylphenyl)ethynyl)picolinonitrile (from Example 47/Step 3) and tert-butyl 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (from Example 5/Step 2) following the procedures described for Example 44, step 4.
Sources & evidence
- ORD record
- ord-530545335b38466b9b120488eabcb362
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895577B2
Reaction notes
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