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

HRID 277967Notes

Reaction equation

HRID 277967 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([C:10](=[O:15])N(C)OC)=[CH:6][N:5]2[C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Br[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=1>>[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([C:10](=[O:15])[C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=3)=[CH:6][N:5]2[C:16]=1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 140821-Bromo-3-fluorobenzeneHCID 226266852-Amino-3-phenyl-6-(N-methyl-N-methoxycarbamoyl)imidazo[1,2-a]pyridine

Product 1

HCID 226267322-Amino-3-phenyl-6-(3-fluorobenzoyl)-imidazo[1,2-a]pyridine

Procedure

The 2-amino-3-phenyl-6-(N-methyl-N-methoxycarbamoyl)imidazo[1,2-a]pyridine (148 mg, 0.500 mmol) and 1-bromo-3-fluorobenzene were converted to product in a manner substantially analogous to Example 141 to give 37 mg. (37%). MS(FAB+) m/z 332.2 (M++1, 86.6), NMR (200 MHz, CDCl3) d 4.22 (bs, 2H, NH), 7.21-7.55 (m, 11H, ArH+H7+H8), 8.69 (d, J57=1.1, H5).

Workup

  1. customto give 37 mg

Sources & evidence

ORD record
ord-f09314bb6cd940549afffa994f967ea9
Source dataset
uspto-grants-2002_03
Patent number
US06358971B1

Reaction notes

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