Sodium Hydroxide → HCID 67960086, compound

HRID 1529450Notes

Reaction equation

HRID 1529450 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[C:14]([C:27]3[N:28]=[N:29][CH:30]=[C:31]([O:33][CH3:34])[CH:32]=3)=[CH:15][N:16](S(C3C=CC(C)=CC=3)(=O)=O)[C:11]2=[CH:10][CH:9]=1.[OH-].[Na+]>C1COCC1.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]2[C:14]([C:27]3[N:28]=[N:29][CH:30]=[C:31]([O:33][CH3:34])[CH:32]=3)=[CH:15][NH:16][C:11]2=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67959633HCID 67959633, compound

Product 1

HCID 67960086HCID 67960086, compoundYield 55.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

A glass microwave reaction vessel was charged with 5-(2-fluorophenyl)-3-(5-methoxypyridazin-3-yl)-1-tosyl-1H-pyrrolo[3,2-b]pyridine (16 mg, 0.034 mmol) and NaOH (0.3 mL, 0.300 mmol, 1M) in THF (1 mL). The reaction was stirred and heated in a Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 85° C. for 20 min. The mixture was diluted with water and extracted with CHCl3/iPrOH (4:1). The combined organic layers were dried, filtered and concentrated. The residue was purified with prep-TLC (eluting with 10% MeOH in DCM) to give 5-(2-fluorophenyl)-3-(5-methoxypyridazin-3-yl)-1H-pyrrolo[3,2-b]pyridine (6.0 mg, 0.019 mmol, 55.6% yield) as a light brown solid. MS (ESI, pos. ion) m/z: 321.0 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 12.05 (1 H, br. s.), 8.83 (2 H, s), 8.60 (1 H, s), 8.12 (1H, td, J=8.0, 1.7 Hz), 8.03 (1 H, d, J=8.6 Hz), 7.70 (1 H, dd, J=8.5, 2.1 Hz), 7.43-7.53 (1 H, m), 7.30-7.42 (2 H, m), 4.01 (3 H, s)

Workup

  1. customA glass microwave reaction vessel
  2. extractionextracted with CHCl3/iPrOH (4:1)
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with prep-TLC (eluting with 10% MeOH in DCM)

Sources & evidence

ORD record
ord-fa266ad64b324c23a97ea2201f19491c
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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