Iodine → HCID 57917491, compound

HRID 69234Notes

Reaction equation

HRID 69234 reaction equation
II.O[PH2]=O.[F:6][C:7]1[C:16]([C:17]([C:20]2[N:24]3[N:25]=[C:26]([C:29]4[CH:30]=[N:31][N:32]([CH3:34])[CH:33]=4)[CH:27]=[CH:28][C:23]3=[N:22][CH:21]=2)(O)[CH3:18])=[C:15]([F:35])[CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2.[OH-].[Na+]>C(O)(=O)C>[F:6][C:7]1[C:16]([CH:17]([C:20]2[N:24]3[N:25]=[C:26]([C:29]4[CH:30]=[N:31][N:32]([CH3:34])[CH:33]=4)[CH:27]=[CH:28][C:23]3=[N:22][CH:21]=2)[CH3:18])=[C:15]([F:35])[CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[N:12]2

Participants

6

Reactant 4

HCID 807IodineHCID 14798Sodium HydroxideHCID 4124402Phosphinic AcidHCID 57917385HCID 57917385, compound

Product 1

HCID 57917491HCID 57917491, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Iodine (723 mg, 2.85 mmol) and H3PO2 (0.777 mL, 14.25 mmol) were added to a solution of (rac)-1-(5,7-difluoro-quinolin-6-yl)-1-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-ethanol (Stage 191.1, 386 mg, 0.950 mmol) in acetic acid (8 mL). The RM was subjected to MW-irradiation at 150° C. for 5 min. The RM was neutralized with 2.5 M NaOH solution and extracted twice with EtOAc. The organics were joined and washed with brine, then dried over Na2SO4 and the solvent was removed. The residue was triturated with Et2O and the precipitate was filtered off to afford the title compound a yellow solid (tR 0.95 min (conditions 2), MH+=391, 1H-NMR in DMSO-d6: 8.90 (d, 1H); 8.49 (d, 1H); 8.18 (s, 1H); 8.04 (d, 1H); 7.81 (s, 1H); 7.67 (d, 1H); 7.56 (dd, 1H); 7.42 (d, 1H); 5.10 (q, 1H); 3.85 (s, 3H); 1.91 (d, 3H)).

Workup

  1. extractionextracted twice with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed
  5. customThe residue was triturated with Et2O
  6. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-5d681c0597d04df18a460c126ac141af
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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