Sodium Carbonate → (E)-2-styrylbenzo[f][1,7]naphthyridin-5-amine

HRID 340230Notes

Reaction equation

HRID 340230 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O)=O)(C)(C)C.Cl[C:19]1[C:20]([C:33]#[N:34])=[N:21][CH:22]=[C:23](/[CH:25]=[CH:26]/[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.CO>[CH:25](/[C:23]1[CH:22]=[N:21][C:20]2[C:19]([CH:24]=1)=[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]1=[N:8][C:33]=2[NH2:34])=[CH:26]\[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2773226(2-BOC-aminophenyl)boronic acidHCID 66875239(E)-3-chloro-5-styrylpicolinonitrile

Product 1

HCID 58213554(E)-2-styrylbenzo[f][1,7]naphthyridin-5-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21863594Toluene ethanolSolvent

Procedure

A solution of 2-(tert-butoxycarbonylamino)phenylboronic acid (1.0 eq.) and (E)-3-chloro-5-styrylpicolinonitrile (from 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 stirred 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 product was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give (E)-2-styrylbenzo[f][1,7]naphthyridin-5-amine as a brown solid. 1H NMR (dmso-d6): δ 9.22 (d, 1H), 9.06 (d, 1H), 8.51 (d, 1H), 7.78 (d, 1H), 7.66 (d, 2H), 7.46-7.56 (m, 3H), 7.70 (t, 2H), 7.26-7.32 (m, 2H), 7.08 (bs, 2H). LRMS [M+H]=298.2.

Workup

  1. filtrationThe insoluble solids were filtered off
  2. concentrationthe filtrate was concentrated en vacuo
  3. customto obtain a crude residue
  4. customThe crude product was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-5495b84df6aa434f94fba1668cd3e66e
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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