Pyridine → HCID 89501294, compound

HRID 64181Notes

Reaction equation

HRID 64181 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[CH:9][N:8]([C:11]3[CH:12]=[C:13]([NH2:25])[CH:14]=[C:15]([C:17]4[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=4[F:24])[CH:16]=3)[C:5]2=[N:6][CH:7]=1.N1C=CC=CC=1.[CH2:32]([S:34](Cl)(=[O:36])=[O:35])[CH3:33]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[CH:9][N:8]([C:11]3[CH:12]=[C:13]([NH:25][S:34]([CH2:32][CH3:33])(=[O:36])=[O:35])[CH:14]=[C:15]([C:17]4[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=4[F:24])[CH:16]=3)[C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 89500107HCID 89500107, compound

Product 1

HCID 89501294HCID 89501294, compoundYield 76.68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(6-bromo-3H-imidazo[4,5-b]pyridin-3-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-amine (133 mg, 0.33 mmol) in DCM was added pyridine (52 mg, 0.66 mmol, 2.0 eq.) followed by ethanesulfonyl chloride (76 mg, 0.66 mmol, 2.0 eq.). The mixture was stirred for 1 h, and quenched and extracted as in Example 2(b). The solvent was distilled off to afford the crude residue which was taken to the next step without further purification, yield 76.68% (125 mg); LC-MS (ESI): Calculated mass: 492.01; Observed mass: 493.0 [M+H]+ (rt: 1.72 min).

Workup

  1. customquenched
  2. extractionextracted as in Example 2(b)
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-90cb35cb6eac45f1a0b3c6d4bdc37a21
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

Loading…