Ethanol → 6-bromo-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide

HRID 1961473Notes

Reaction equation

[NH2:1][C:2]1[N:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[CH:4]=O.[C:11]([C:15]1[CH:28]=[CH:27][C:18]([CH2:19][NH:20][C:21](=[O:26])[CH2:22][C:23](=O)[CH3:24])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].CCO>N1CCCCC1.O>[Br:10][C:7]1[CH:6]=[C:3]2[C:2](=[N:9][CH:8]=1)[N:1]=[C:23]([CH3:24])[C:22]([C:21]([NH:20][CH2:19][C:18]1[CH:17]=[CH:16][C:15]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:28][CH:27]=1)=[O:26])=[CH:4]2

Participants

Conditions

Temperature: 120 °C

Procedure

2-Amino-5-bromonicotinaldehyde (0.50 g, 2.49 mmol) and N-(4-tert-butylbenzyl)-3-oxobutanamide (0.62 g, 2.49 mmol) were suspended in piperidine (1.0 ml) and EtOH (1.0 ml) in a high-pressure vial. The mixture was heated at 120° C. for 4.5 hours and then cooled to room temperature. The reaction was diluted with water (40 ml) and extracted with CH2Cl2 (3*30 ml). Combined organics were washed with water (30 ml), dried over MgSO4 and evaporated. The crude product was purified by flash chromatography using CH2Cl2/CH3OH (20:1) as eluent to give 0.56 g (54%) of 6-bromo-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide as yellow solids.

Workup

temperaturecooled to room temperature
extractionextracted with CH2Cl2 (3*30 ml)
washCombined organics were washed with water (30 ml)
dry with materialdried over MgSO4
customevaporated
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-d180a1679ada4d5397df4935c395e6ed
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415333B2

Reaction notes

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