Trimethylsilyl iodide → HCID 68291912, compound

HRID 877834Notes

Reaction equation

HRID 877834 reaction equation
[I:1][Si](C)(C)C.[Br:6][C:7]1[CH:8]=[C:9]2[C:14]([NH:15][C@@H:16]3[CH2:20][N:19](C(OCC4C=CC=CC=4)=O)[CH2:18][C@@:17]3([F:32])[CH3:31])=[C:13]([C:33](=[O:35])[NH2:34])[CH:12]=[N:11][N:10]2[CH:36]=1>C(#N)C>[IH:1].[Br:6][C:7]1[CH:8]=[C:9]2[C:14]([NH:15][C@H:16]3[C@:17]([F:32])([CH3:31])[CH2:18][NH:19][CH2:20]3)=[C:13]([C:33]([NH2:34])=[O:35])[CH:12]=[N:11][N:10]2[CH:36]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 68350417HCID 68350417, compound

Product 1

HCID 68291912HCID 68291912, compoundYield 105.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Iodotrimethylsilane (0.134 mL, 0.938 mmol) was added dropwise to a solution of (3S,4R)-benzyl 4-((6-bromo-3-carbamoylpyrrolo[1,2-b]pyridazin-4-yl)amino)-3-fluoro-3-methylpyrrolidine-1-carboxylate (115 mg, 0.235 mmol) in acetonitrile (3 mL). After 1 h at room temperature, the mixture was quenched with methanol (1 mL) and concentrated in vacuo. The solid residue was triturated with diethyl ether (3 mL) and filtered. The filter cake was rinsed with diethyl ether and dried under vacuum to give crude 6-bromo-4-(((3R,4S)-4-fluoro-4-methylpyrrolidin-3-yl)amino)pyrrolo[1,2-b]pyridazine-3-carboxamide hydroiodide (120 mg), which was used in the next step without further purification. MS (ES+) m/z: 356.0 (M+H).

Workup

  1. customthe mixture was quenched with methanol (1 mL)
  2. concentrationconcentrated in vacuo
  3. customThe solid residue was triturated with diethyl ether (3 mL)
  4. filtrationfiltered
  5. washThe filter cake was rinsed with diethyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-19a5cca40d7c4f5d9622beffb57221fa
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

Loading…