Sodium Hydroxide → 4-bromo-N-(4-methoxybenzyl)picolinamide

HRID 572642Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.[CH3:44][O:45][C:46]1[CH:51]=[CH:50][C:49]([CH2:52][NH2:53])=[CH:48][CH:47]=1.[OH-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:53][CH2:52][C:49]2[CH:50]=[CH:51][C:46]([O:45][CH3:44])=[CH:47][CH:48]=2)=[O:10])[CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a flask containing a 4-bromopicolinic acid (1.0 g) in DMF (10 mL) was added HATU (2.3 g) and N-ethyl-N-isopropylpropan-2-amine (1.0 mL) The mixture was stirred at about 25° C. for approximately 10 min followed by addition of (4-methoxyphenyl)methanamine (0.68 g). The reaction was then stirred at about 25° C. for about an additional 12 h. The reaction was basified to pH 10 with aqueous 1 N NaOH and washed three times with EtOAc. The organic solution was dried over MgSO4, filtered, and concentrated under reduced pressure to afford 4-bromo-N-(4-methoxybenzyl)picolinamide as a clear oil (1.2 g, 75%). LC/MS (Table 1, method f). Rt=1.73 min; MS m/z 322 (M+H)+.

Workup

stirringThe reaction was then stirred at about 25° C. for about an additional 12 h
washwashed three times with EtOAc
dry with materialThe organic solution was dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-297c5b2b9d2e46d6b34961d6760b7803
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029409B2

Reaction notes

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