Iodine → HCID 57917487, compound

HRID 69205Notes

Reaction equation

HRID 69205 reaction equation
[F:1][C:2]1[C:3]([C:19]([C:22]2[N:26]3[N:27]=[C:28]([C:31]4[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=4)[CH:29]=[CH:30][C:25]3=[N:24][CH:23]=2)(O)[CH3:20])=[CH:4][C:5]2[C:9]([CH:10]=1)=[N:8][N:7](COCC[Si](C)(C)C)[CH:6]=2.FC1C=C2C(C=NN2COCC[Si](C)(C)C)=CC=1C(C1N2N=C(C3C=NN(C)C=3)C=CC2=NC=1)(O)C.II.O[PH2]=O>C(O)(=O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[CH:19]([C:22]1[N:26]2[N:27]=[C:28]([C:31]3[CH:32]=[N:33][N:34]([CH3:36])[CH:35]=3)[CH:29]=[CH:30][C:25]2=[N:24][CH:23]=1)[CH3:20]

Participants

6

Reactant 4

HCID 807IodineHCID 4124402Phosphinic AcidHCID 68631442(Rac)-1-[6-fluoro-2-(2-trimethylsilanyl-ethoxymethyl)-2h-indazol-5-yl]-1-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-ethanolHCID 68640315(Rac)-1-[6-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1h-indazol-5-yl]-1-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-ethanol

Product 1

HCID 57917487HCID 57917487, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of (rac)-1-[6-Fluoro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-indazol-5-yl]-1-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-ethanol and (rac)-1-[6-Fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-5-yl]-1-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-ethanol (Stage 164.1, 563 mg, 1.109 mmol), iodine (844 mg, 3.33 mmol), H3PO2 (1.815 mL of a 50% aqueous solution, 16.64 mmol) and acetic acid (9.5 mL) were introduced in a microwave tube and the mixture was subjected to MW-irradiation at 150° C. for 5 min. The solvent was removed and the residue was taken up with 1 N HCl and washed with EtOAc three times. The aqueous layer was basified with NaOH pellets and extracted twice with EtOAc. The organics were joined and washed with brine, dried over Na2SO4 and the solvent was removed. The title compound was obtained as a racemic mixture (tR 1.0 min (conditions 2), MH+=362).

Workup

  1. additionwere introduced in a microwave tube
  2. customThe solvent was removed
  3. washwashed with EtOAc three times
  4. extractionextracted twice with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-2bef876e7a594495a363751dcba17381
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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