Water → 2-Amino-3-phenyl-6-(2-fluorobenzoyl)-imidazo[1,2-a]pyridine

HRID 277966Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[F:8].C([Li])(C)(C)C.[NH2:14][C:15]1[N:16]=[C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:28])N(C)OC)=[CH:19][N:18]2[C:29]=1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>C1COCC1>[NH2:14][C:15]1[N:16]=[C:17]2[CH:22]=[CH:21][C:20]([C:23](=[O:28])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[F:8])=[CH:19][N:18]2[C:29]=1[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 1-bromo-2-fluorobenzene (191 mL, 1.75mmol) in dry THF (2 mL) under an argon atmosphere was added t-butyl lithium dropwise. After stirring for 50 minutes at −78° C., a solution of 2-amino-3-phenyl-6-(N-methyl-N-methoxycarbamoyl)imidazo[1,2-a]pyridine (148 mg, 0.5 mmol) in dry THF (3 mL) was added. The resulting red-orange solution was stirred at the same temperature for another 50 minutes and then allowed to warm to RT. The solution was poured into H2O (20 mL) and extracted with EtOAc (2×20 mL). The organic layer was washed with H2O, dried (Na2SO4), and removed in vacuo to give a brown solid. The crude solid was purified by column chromatography (CH2Cl2/CH3CN 2.5/1) to give 84.0 mg (50.6%) of product as a yellow solid. MS(FAB) m/z 332.2 (M++1, 51.99), NMR (200 MHz, CDCl3) d 4.27 (bs, 2H, NH), 7.12-7.58 (m, 11H, ArH+H7+H8), 8.71 (s, H5).

Workup

stirringThe resulting red-orange solution was stirred at the same temperature for another 50 minutes
temperatureto warm to RT
extractionextracted with EtOAc (2×20 mL)
washThe organic layer was washed with H2O
dry with materialdried (Na2SO4)
customremoved in vacuo
customto give a brown solid
customThe crude solid was purified by column chromatography (CH2Cl2/CH3CN 2.5/1)

Sources & evidence

ORD record: ord-0d9a0919522248cca37fcab1290b906b
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358971B1

Reaction notes

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