Pyridine → HCID 117777734, compound

HRID 64186Notes

Reaction equation

HRID 64186 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.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>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:33]([CH3:32])(=[O:35])=[O:34])[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 31297Methanesulfonyl chlorideHCID 89500107HCID 89500107, compound

Product 1

HCID 117777734HCID 117777734, compoundYield 75%

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 methanesulfonyl chloride (76 mg, 0.66 mmol, 2 eq.). The reaction 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 next step without further purification. Yield 75.0% (120 mg). 1H NMR (300 MHz, DMSO-d6): δ 10.30 (s, 1H), 9.30 (s, 1H), 8.56 (s, 1H), 7.83 (s, 1H), 7.45 (s, 1H), 7.44 (s, 2H), 3.16 (s, 3H); LC-MS (ESI): Calculated mass: 479.5; Observed mass: 480.2 [M+H]+ (rt: 1.59 min).

Workup

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

Sources & evidence

ORD record
ord-d778bf52f31e48fd869f408cd4c5cb43
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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