Acetic Acid → Methyl 2-{[(2-bromopyridin-4-yl)methyl]amino}benzoate

HRID 2110177Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:11])[C:4]1[C:5](=[CH:7][CH:8]=[CH:9][CH:10]=1)[NH2:6].C(O)(=O)C.[Br:16][C:17]1[CH:22]=[C:21]([CH:23]=O)[CH:20]=[CH:19][N:18]=1.C([BH3-])#N.[Na+]>CO.O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][CH2:23][C:21]1[CH:20]=[CH:19][N:18]=[C:17]([Br:16])[CH:22]=1

Participants

Conditions

Temperature: 40 °C

Procedure

6.04 g (40 mmol) of anthranilic acid methyl ester in 600 ml of methanol is mixed with 3.2 ml of acetic acid and 7.4 g (40 mmol) of 2-bromopyridine-4-carbaldehyde, and it is stirred overnight at 40° C. 3.8 g (60 mmol) of sodium cyanoborohydride is added thereto and stirred overnight at 40° C. 3.8 g (60 mmol) of sodium cyanoborohydride is added again and stirred over the weekend at 40° C. It is mixed with water and largely concentrated by evaporation. The aqueous phase is extracted with ethyl acetate, and the combined organic phases are dried, filtered and concentrated by evaporation. The crude product is chromatographed on silica gel with a gradient that consists of hexane and hexane/ethyl acetate 1:3 and hexane/ethyl acetate 1:1 as an eluant. 10.0 g (78% of theory) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-benzoic acid methyl ester is obtained as a colorless oil.

Workup

stirringstirred overnight at 40° C
stirringstirred over the weekend at 40° C
concentrationlargely concentrated by evaporation
extractionThe aqueous phase is extracted with ethyl acetate
customthe combined organic phases are dried
filtrationfiltered
concentrationconcentrated by evaporation
customThe crude product is chromatographed on silica gel with a gradient that

Sources & evidence

ORD record: ord-95d38dc6e5ec4c05aab94b43d2c0f706
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517894B2

Reaction notes

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