4-Methylmorpholine → N-(3-Bromopyridin-2-yl)-5-(((4-methoxybenzyl)oxy)methyl)furo[2,3-b]pyridine-2-carboxamide

HRID 931388Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][O:8][CH2:9][C:10]2[CH:11]=[C:12]3[CH:18]=[C:17]([C:19]([OH:21])=O)[O:16][C:13]3=[N:14][CH:15]=2)=[CH:5][CH:4]=1.[Br:24][C:25]1[C:26]([NH2:31])=[N:27][CH:28]=[CH:29][CH:30]=1.CN1CCOCC1.F[P-](F)(F)(F)(F)F.CN(C)C(Cl)=[N+](C)C>CN(C=O)C>[Br:24][C:25]1[C:26]([NH:31][C:19]([C:17]2[O:16][C:13]3=[N:14][CH:15]=[C:10]([CH2:9][O:8][CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:23][CH:22]=4)[CH:11]=[C:12]3[CH:18]=2)=[O:21])=[N:27][CH:28]=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 70 °C

Procedure

In an oven-dried sealed tube, a mixture of 5-(((4-methoxybenzyl)-oxy)methyl)furo[2,3-b]pyridine-2-carboxylic acid (2.0 g, 6.4 mmol), 3-bromo-2-amino pyridine (3.31 g, 19.2 mmol), N-methyl morpholine (1.93 g, 19.2 mmol) and N,N,N′,N′-tetramethylchloroformamidinium hexafluorophosphate (3.58 g, 12.8 mmol) in DMF (20 mL) was heated to 70° C. for 5 h. The reaction mixture was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in petroleum ether to give the title compound. MS: m/z=468.5 (M+1).

Workup

customIn an oven-dried sealed tube
customThe reaction mixture was partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate
washThe organic layer was washed with water, brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-2cdc9a834ef840699759a548ccfcb69e
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296750B2

Reaction notes

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