Sodium Carbonate → 8-Methyl-2-vinylbenzo[f][1,7]naphthyridin-5-amine

HRID 340244Notes

Reaction equation

HRID 340244 reaction equation
[CH3:1][C:2]1C=CC(B2OC(C)(C)C(C)(C)O2)=C(NC(=O)OC(C)(C)C)C=1.[CH:25]1[C:34]2[C:29](=[C:30]([NH2:39])[N:31]=[C:32]3[CH:38]=[CH:37][CH:36]=[CH:35][C:33]3=2)[N:28]=[CH:27][CH:26]=1.[C:40](=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.CO>[CH3:40][C:37]1[CH:36]=[CH:35][C:33]2=[C:34]3[C:29](=[C:30]([NH2:39])[N:31]=[C:32]2[CH:38]=1)[N:28]=[CH:27][C:26]([CH:1]=[CH2:2])=[CH:25]3

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10910433Benzo[f][1,7]naphthyridin-5-amineHCID 46737997tert-Butyl (5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate

Product 1

HCID 582136748-Methyl-2-vinylbenzo[f][1,7]naphthyridin-5-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21863594Toluene ethanolSolvent

Procedure

A solution of tert-butyl 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (from Example 5/step 2) (1.0 eq.) and 3-chloro-5-vinylpicolinonitrile (from Example 29/Step 1) (1.0 eq.), tetrakis(triphenyl-phosphine)palladium (5 mol %), and 2N aqueous sodium carbonate solution (2.0 eq.) in toluene/ethanol (2:1, 0.03 M) was stiffed at 100° C. overnight. After cooling to ambient temperature, the reaction content was diluted with methanol. The insoluble solids were filtered off, and the filtrate was concentrated en vacuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give 8-methyl-2-vinylbenzo[f][1,7]naphthyridin-5-amine as a yellow solid.

Workup

  1. customwas stiffed at 100° C. overnight
  2. filtrationThe insoluble solids were filtered off
  3. concentrationthe filtrate was concentrated en vacuo
  4. customto obtain a crude residue
  5. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-d4ce9f1c17864a79a51ae92ab0803b87
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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