Sodium Carbonate → 2-Phenylbenzo[f][1,7]naphthyridin-5-amine

HRID 340228Notes

Reaction equation

HRID 340228 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:31]#[N:32])=[N:21][CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.CO>[C:25]1([C:23]2[CH:22]=[N:21][C:20]3[C:19]([CH:24]=2)=[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=[N:8][C:31]=3[NH2:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2773226(2-BOC-aminophenyl)boronic acidHCID 668755223-Chloro-5-phenylpicolinonitrile

Product 1

HCID 582137172-Phenylbenzo[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 3-chloro-5-phenylpicolinonitrile (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 2-phenylbenzo[f][1,7]naphthyridin-5-amine as a white solid. 1H NMR (dmso-d6): δ 9.13 (d, 1H), 9.03 (d, 1H), 8.56 (d, 1H), 7.98 (d, 2H), 7.43-7.56 (m, 5H), 7.27 (m, 1H), 7.13 (bs, 2H). LRMS [M+H]=272.2.

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-e3446919bd0347dbb0474b74fa71e01b
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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