Water → 3-[(7-Bromo-imidazo[1,2-a]pyridine-3-carbonyl)-amino]-4-fluoro-benzoic Acid Methyl Ester

HRID 335274Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([OH:13])=O)=[CH:9][N:10]=[C:4]2[CH:3]=1.O=S(Cl)Cl.[NH2:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[F:29])[C:22]([O:24][CH3:25])=[O:23].O>CC(N(C)C)=O>[CH3:25][O:24][C:22](=[O:23])[C:21]1[CH:26]=[CH:27][C:28]([F:29])=[C:19]([NH:18][C:11]([C:8]2[N:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]3=[N:10][CH:9]=2)=[O:13])[CH:20]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To the solution of compound 7-bromoimidazo[1,2-a]pyridine-3-carboxylic acid (Intermediate A step 3) (1.26 Kg, 5.23 mol) in DMAC (15 L) was added dropwise SOCl2 (1.86 kg, 15.6 mol) at 10° C. in 30 min. To the resulting mixture warmed to 20° C. was added compound methyl 3-amino-4-fluorobenzoate (884 g, 5.23 mol) in DMAC (3.0 L) over 30 min. After addition, the reaction temperature went up to 30° C. HPLC showed the reaction went to completion within 5 min. To the reaction mixture was added water (20 L) over 20 min. The mixture was filtered and dried under vacuum to afford the title compound as a white solid;

Workup

additionAfter addition
customwent up to 30° C
filtrationThe mixture was filtered
customdried under vacuum

Sources & evidence

ORD record: ord-8ec7e2ae840146db969d4d9076d79abb
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883819B2

Reaction notes

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