Ethyl Acetate → HCID 59596521, compound

HRID 2264946Notes

Reaction equation

HRID 2264946 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[CH:12]=[CH:11][N:10]=[N:9][C:8]=2[C:7]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([Si](C)(C)C)=[CH:19][C:18]=1[F:27])=[O:5])[CH3:2].[I:28]Cl.C(OCC)(=O)C>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH3:15])[C:13]2[CH:12]=[CH:11][N:10]=[N:9][C:8]=2[C:7]=1[NH:16][C:17]1[CH:22]=[CH:21][C:20]([I:28])=[CH:19][C:18]=1[F:27])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24640Iodine chlorideHCID 59596610HCID 59596610, compound

Product 1

HCID 59596521HCID 59596521, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (0° C.) solution 7-(2-fluoro-4-trimethylsilanyl-phenylamino)-5-methyl-5H-pyrrolo[3,2-c]pyridazine-6-carboxylic acid ethyl ester (242 mg, 0.626 mmol) in DCM (6 mL) was added iodine monochloride (1.25 mL 1M in DCM 17.0 mL) dropwise over 1 minute. The mixture was allowed to warm to ambient temperature, stirred for 1 hour, then partitioned between ethyl acetate and a saturated solution of sodium thiosulfate. The organic layer was separated, washed with water, dried (Na2SO4), filtered and evaporated to give a residue. The residue was subjected to flash chromatography (Si-PPC, 1:1 DCM:ethyl acetate eluent) to provide the title compound as an orange solid (242 g, 88%). LCMS (method B): RT=3.03 min, M+H+=441.

Workup

  1. custompartitioned between ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue

Sources & evidence

ORD record
ord-7c62a200e57540cf9d7e13344546d5ce
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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