1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Fluoro-5-(3-(oxazol-5-yl)pyridin-2-yloxy)benzoic acid

HRID 883030Notes

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[C:17]([CH:18]=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CC1C=CC(S([CH2:30][N+:31]#[C-:32])(=O)=O)=CC=1.C1CCN2C(=NCCC2)CC1>COCCOC>[F:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[C:17]([C:18]3[O:19][CH:32]=[N:31][CH:30]=3)=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 85 °C

Procedure

To 2-fluoro-5-(3-formylpyridin-2-yloxy)benzoic acid (230 mg, 0.881 mmol) and TosMIC (172 mg, 0.881 mmol) in DME (8.0 mL) was added DBU (0.29 mL, 1.9 mmol). The mixture was heated to 85° C. for 2.5 hours in a sealed tube. After concentrated, the residue was diluted with saturated sodium carbonate and extracted with EtOAc. The aqueous layer was acidified with TFA (pH˜3) and the resulting solid was filtered and dried to yield 2-fluoro-5-(3-(oxazol-5-yl)pyridin-2-yloxy)benzoic acid as a beige solid. MS m/z=301 [M+1]+. Calc'd for C15H9FN2O4: 300.25.

Workup

concentrationAfter concentrated
additionthe residue was diluted with saturated sodium carbonate
extractionextracted with EtOAc
filtrationthe resulting solid was filtered
customdried

Sources & evidence

ORD record: ord-09f979db78754641836bc59f977a8fdd
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236823B2

Reaction notes

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