Sodium Carbonate → Methyl 5-aminobenzo[f][1,7]naphthyridine-8-carboxylate

HRID 1259166Notes

Reaction equation

HRID 1259166 reaction equation
C(OC([NH:8]C1C=C(C(OC)=O)C=CC=1B(O)O)=O)(C)(C)C.Br[C:23]1[C:24]([C:29]#[N:30])=[N:25][CH:26]=[CH:27][CH:28]=1.[C:31](=[O:34])([O-])[O-].[Na+].[Na+].[C:37]1([CH3:43])C=C[CH:40]=[CH:39][CH:38]=1.[CH2:44]([OH:46])[CH3:45]>>[NH2:8][C:29]1[C:24]2[N:25]=[CH:26][CH:27]=[CH:28][C:23]=2[C:38]2[CH:39]=[CH:40][C:45]([C:44]([O:34][CH3:31])=[O:46])=[CH:43][C:37]=2[N:30]=1

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 8176943-Bromopyridine-2-carbonitrileHCID 21863594Toluene ethanolHCID 668752372-(Tert-butoxycarbonylamino)-4-(methoxycarbonyl)phenylboronic acid

Product 1

HCID 66875226Methyl 5-aminobenzo[f][1,7]naphthyridine-8-carboxylate

Procedure

A solution of 2-(tert-butoxycarbonylamino)-4-(methoxycarbonyl) phenylboronic acid (from the previous step) (1.0 eq.) and 3-bromopicolinonitrile (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 mixture was filtered to collect the precipitate. The precipitate was rinsed with EtOAc to give methyl 5-aminobenzo[f][1,7]naphthyridine-8-carboxylate as a pale brown solid.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customto collect the precipitate
  3. washThe precipitate was rinsed with EtOAc

Sources & evidence

ORD record
ord-f1467873f1ee408cbf87617a6dad6f7d
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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