Sodium Methoxide → 5-[[2-[N-(6-Bromopyridin-2-yl)amino]thiazol-5-yl]thio]-2-methylbenzoic acid

HRID 1294751Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[S:10][C:11](Br)=[CH:12][N:13]=2)[CH:5]=[CH:4][CH:3]=1.[C:15]([C:18]1[CH:19]=[C:20]([SH:25])[CH:21]=[CH:22][C:23]=1[CH3:24])([OH:17])=[O:16].C[O-].[Na+]>CO.C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[S:10][C:11]([S:25][C:20]3[CH:21]=[CH:22][C:23]([CH3:24])=[C:18]([CH:19]=3)[C:15]([OH:17])=[O:16])=[CH:12][N:13]=2)[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 54 °C

Procedure

A suspension of 2-[(6-bromo-2-pyridinyl)amino]-5-bromothiazole (100 mg, 0.3 mmol), 3-carboxy-4-methylthiophenol (170 mg, 0.98 mmol) and sodium methoxide (210 μL, 25% w/w solution in methanol, 0.9 nmuol) in methanol (4.9 mL) and THF (2 mL) was heated to 54° C. for 5.5 h. Supplemental sodium methoxide solution (1.42 mL) was added in portions over a period of 5 h. The mixture was heated to 54° C. for 16 h and concentrated. The residue was diluted with 1 N aqueous HCl solution at 0° C. and stirred for several minutes. The precipitated solid was filtered, washed several times with water and ether, and dried in vacuo over P2O5. Trituration with ether afforded the titled compound (103 mg, 81%) as an off-white solid.

Workup

temperatureThe mixture was heated to 54° C. for 16 h
concentrationconcentrated
additionThe residue was diluted with 1 N aqueous HCl solution at 0° C.
filtrationThe precipitated solid was filtered
washwashed several times with water and ether
dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record: ord-692ac198a3f34d74aabfc3967e6d1a7e
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07241781B2

Reaction notes

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