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Iodine → HCID 57917305, compound

HRID 69206
Notes
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Reaction equation

HRID 69206 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2COCC[Si](C)(C)C)=[CH:4][C:3]=1[CH:19]([C:21]1[N:25]2[N:26]=[C:27]([C:30]3[CH:31]=[N:32][N:33]([CH3:35])[CH:34]=3)[CH:28]=[CH:29][C:24]2=[N:23][CH:22]=1)O.FC1C(C(C2N3N=C(C4C=NN(C)C=4)C=CC3=NC=2)O)=CC2C(C=1)=NN(COCC[Si](C)(C)C)C=2.II.O[PH2]=O>>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[CH2:19][C:21]1[N:25]2[N:26]=[C:27]([C:30]3[CH:31]=[N:32][N:33]([CH3:35])[CH:34]=3)[CH:28]=[CH:29][C:24]2=[N:23][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 807IodineHCID 4124402Phosphinic AcidHCID 68640065(Rac)-[6-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1h-indazol-5-yl]-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanolHCID 68640136(Rac)-[6-fluoro-2-(2-trimethylsilanyl-ethoxymethyl)-2h-indazol-5-yl]-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanol

Product 1

HCID 57917305
HCID 57917305, compound

Procedure

A mixture of (rac)-[6-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-5-yl]-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanol and (rac)-[6-fluoro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-indazol-5-yl]-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanol (Stage 164.3, 400 mg, 0.810 mmol), iodine (617 mg, 2.431 mmol) and H3PO2 (1.326 mL of a 50% aqueous solution, 12.16 mmol) 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 with EtOAc/MeOH (9:1) three times. 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 give the title compound as a light yellow solid (tR 0.90 min (conditions 2), MH+=348, 1H-NMR in DMSO-d6: 13.00 (s, 1H); 8.40 (s, 1H); 8.05 (m, 2H); 7.75 (d, 1H); 7.55 (m, 2H); 7.32 (d, 1H)).

Workup

  1. additionwere introduced in a microwave tube
  2. customThe solvent was removed
  3. washwashed with EtOAc three times
  4. extractionextracted with EtOAc/MeOH (9:1) three times
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent was removed
  8. customThe residue was purified by MPLC with DCM and MeOH

Sources & evidence

ORD record
ord-b8544e40055c48a7803e3b63dbf8a8c1
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822468B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes