Methylorthoformate → 6-fluoro-5-methyl-1-piperidin-4-yl-1H-benzoimidazole

HRID 1716607Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[C:19]([F:21])[C:18]([CH3:22])=[CH:17][C:16]=2[NH2:23])[CH2:10][CH2:9]1)=O)(C)(C)C.[CH:24]([O-])([O-])OC>C(O)=O>[F:21][C:19]1[C:18]([CH3:22])=[CH:17][C:16]2[N:23]=[CH:24][N:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[C:15]=2[CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(2-amino-5-fluoro-4-methyl-phenylamino)piperidine-1-carboxylic acid tert-butyl ester (250 mg, 0.309 mmol) in formic acid (3 mL) was added methyl orthoformate (0.5 mL). After heating for 3 hours at 60° C., the volatiles was removed under reduced pressure to afford crude product 6-fluoro-5-methyl-1-piperidin-4-yl-1H-benzoimidazole (180 mg, 99%) as a brown solid.

Workup

customthe volatiles was removed under reduced pressure

Sources & evidence

ORD record: ord-4a032e76b0244c44abc2b804fd1ca7a7
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803816B2

Reaction notes

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