Sodium Hydroxide → HCID 178505938, compound

HRID 658408Notes

Reaction equation

HRID 658408 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])[C:17]=1[C:18]1[N:19]=[N:20][NH:21][C:22]=1[Si](C)(C)C>CO>[F:3][C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[NH:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])[C:17]=1[C:18]1[N:19]=[N:20][NH:21][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178504169HCID 178504169, compound

Product 1

HCID 178505938HCID 178505938, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

NaOH (50 μL, 2.0 M in H2O, 0.09 mmol) was added to a solution of (2-fluoro-4-iodo-phenyl)-[5-(2-fluoro-phenyl)-4-(5-trimethylsilanyl-1H-[1,2,3]triazol-4-yl)-pyridin-3-yl]-amine (10 mg, 0.02 mmol) in MeOH (1 mL), and stirred overnight at 50° C. The reaction was quenched with satd. NH4Cl, diluted with EtOAc, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 0 to 75% EtOAc in hexanes to afford the desired product (6 mg, 69%) as a yellow solid. LC-MS (M+H=476, obsd.=476). 1H NMR: δ 8.51 (s, 1H), 8.19 (s, 1H), 7.62 (dd, 1H), 7.44 (m, 1H), 7.38 (m, 2H), 7.28 (m, 2H), 7.19 (t, 1H), 6.99 (s, 1H).

Workup

  1. customThe reaction was quenched with satd
  2. additionNH4Cl, diluted with EtOAc
  3. filtrationfiltered through an Extrelut column
  4. washThe column was washed with EtOAc
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was purified via Biotage
  7. washeluting with a gradient of 0 to 75% EtOAc in hexanes

Sources & evidence

ORD record
ord-ce8b539d8c384c39a010f6e0b1e2829f
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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