Triacetoxyperiodinane → (Rac)-3-[1-(6-fluoro-1-methyl-1h-indazol-5-yl)-ethyl]-6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

HRID 69281Notes

Reaction equation

HRID 69281 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][C:21]=3[F:22])[N:18]([CH3:23])[N:17]=[CH:16]4)O)=[CH:9][N:10]=2)[N:7]=1.ClC1C=CC2N(C(C(C3C=[C:38]4[C:42](=CC=3F)[N:41]([CH3:46])[N:40]=[CH:39]4)=O)=CN=2)N=1.[CH3:47]C(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:22][C:21]1[CH:20]=[C:19]2[C:15]([CH:16]=[N:17][N:18]2[CH3:23])=[CH:14][C:13]=1[CH:11]([C:8]1[N:6]2[N:7]=[C:2]([C:38]3[CH:39]=[N:40][N:41]([CH3:46])[CH:42]=3)[CH:3]=[CH:4][C:5]2=[N:10][CH:9]=1)[CH3:47]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 131731820(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(6-fluoro-1-methyl-1H-indazol-5-yl)-methanone (rac)-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(6-fluoro-1-methyl-1H-indazol-5-yl)-methanol

Product 1

HCID 57917432(Rac)-3-[1-(6-fluoro-1-methyl-1h-indazol-5-yl)-ethyl]-6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(6-fluoro-1-methyl-1H-indazol-5-yl)-methanone (rac)-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(6-fluoro-1-methyl-1H-indazol-5-yl)-methanol (Stage 278.4, 4.2 g, 12.66 mmol) was suspended in DCM (250 mL). Dess-Martin periodinane (10.64 g, 38.0 mmol) was added and the mixture was stirred at rt for 1.5 h. The mixture was evaporated to dryness and the residue was taken in 1 M NaOH and sonicated. After 15 min of stirring, it was filtered. The precipitate was dried under vacuum overnight to afford the title compound (tR 1.13 min (conditions 2), MH+=330)

Workup

  1. customThe mixture was evaporated to dryness
  2. customsonicated
  3. stirringAfter 15 min of stirring
  4. filtrationit was filtered
  5. customThe precipitate was dried under vacuum overnight

Sources & evidence

ORD record
ord-a13de345a6974dab8fedd4a3fc22da45
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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