Sodium Hydroxide → (5,7-Difluoro-quinolin-6-yl)-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanone

HRID 69236Notes

Reaction equation

HRID 69236 reaction equation
[F:1][C:2]1[C:11]([CH:12]([C:14]2[N:18]3[N:19]=[C:20]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)[CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)[OH:13])=[C:10]([F:29])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl>[F:1][C:2]1[C:11]([C:12]([C:14]2[N:18]3[N:19]=[C:20]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)[CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)=[O:13])=[C:10]([F:29])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 68640982(Rac)-(5,7-difluoro-quinolin-6-yl)-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanol

Product 1

HCID 68633265(5,7-Difluoro-quinolin-6-yl)-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(rac)-(5,7-Difluoro-quinolin-6-yl)-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanol (Stage 191.3, 1.0 g, 2.55 mmol) was dissolved in DCM (25.5 mL) and Dess-Martin periodinane (1.621 g, 3.82 mmol) was added. The RM was stirred for 1 h at rt and then 2.5 M NaOH solution was added. The RM was extracted with EtOAc/MeOH (9:1) twice. The organics were joined and washed with brine, dried over Na2SO4 and the solvent was removed. The residue was purified by MPLC with DCM and MeOH to afford a light yellow solid as the title compound (tR 1.2 min (conditions 2), MH+=391)

Workup

  1. extractionThe RM was extracted with EtOAc/MeOH (9:1) twice
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed
  5. customThe residue was purified by MPLC with DCM and MeOH

Sources & evidence

ORD record
ord-07957fc0db58469da93fdcb5c40bdc63
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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