Iodine → HCID 67111148, compound

HRID 540788Notes

Reaction equation

HRID 540788 reaction equation
II.[CH2:3]([N:5]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][C:14]([CH:17]=O)=[CH:13][CH:12]=2)=[CH:8][C:7]([C:19]2[CH:20]=[C:21]([C:25]3([NH:29][S:30]([CH2:33][C:34]([F:37])([F:36])[F:35])(=[O:32])=[O:31])[CH2:28][O:27][CH2:26]3)[CH:22]=[CH:23][CH:24]=2)=[N:6]1)[CH3:4].[O-]S([O-])(=S)=O.[Na+].[Na+].[NH4+:45].[OH-]>C1COCC1>[C:17]([C:14]1[CH:13]=[CH:12][C:11]([O:10][C:9]2[N:5]([CH2:3][CH3:4])[N:6]=[C:7]([C:19]3[CH:20]=[C:21]([C:25]4([NH:29][S:30]([CH2:33][C:34]([F:36])([F:35])[F:37])(=[O:31])=[O:32])[CH2:28][O:27][CH2:26]4)[CH:22]=[CH:23][CH:24]=3)[CH:8]=2)=[CH:16][CH:15]=1)#[N:45]

Participants

6

Reactant 4

HCID 807IodineHCID 14923Ammonium HydroxideHCID 24477Sodium ThiosulfateHCID 86677199HCID 86677199, compound

Product 1

HCID 67111148HCID 67111148, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Iodine (17.5 mg, 0.069 mmol, 1.3 equiv) was added to a stirring biphasic solution of N-(3-{3-[1-ethyl-5-(4-formylphenoxy)-1H-pyrazol-3-yl]phenyl}oxetane-3-yl)-2,2,2-trifluoroethanesulfonamide (27 mg, 0.053 mmol, 1.0 equiv) in 1 mL THF and 0.53 mL of concentrated NH4OH (28% solution). After stirring for 7 hours, aqueous Na2S2O3 was added (1 mL of a 5% solution) and the reaction mixture was extracted with diethyl ether. The organic layer was dried over magnesium sulfate. The dried solution was filtered and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (0-60% ethyl acetate:hexanes) to give N-(3-{3-[5-(4-cyanophenoxy)-1-ethyl-1H-pyrazol-3-yl]phenyl}oxetane-3-yl)-2,2,2-trifluoroethanesulfonamide (17 mg, 0.034 mmol, 65% yield). HRMS Calc'd (M+1)+507.1308. Found: 507.1305. (400 MHz, 1H, δ-CDCl3) 1.45 (3H, t, J=7.2), 3.04 (2H, q, J=8.6), 4.10 (2H, q, J=7.2), 5.04 (2H, d, J=7.1), 5.16 (2H, d, J=7.1), 5.66 (1H, br s), 6.11 (1H, s), 7.22 (2H, d, H=8.6), 7.36 (1H, d, J=7.9), 7.51 (1H, t, J=8.0), 7.70 (2H, d, J=8.6), 7.80 (2H, m).

Workup

  1. extractionwas extracted with diethyl ether
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationThe dried solution was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by flash chromatography on silica gel (0-60% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-b9e0ac8bf45a4da88c0f3cafa562bfa9
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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