Iodine → HCID 59596235, compound

HRID 2264767Notes

Reaction equation

HRID 2264767 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH3:10])[CH:3]=1.[Mg].II.[Br:14][C:15]1[CH:16]=[C:17]([C:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]#[N:37])=[N:23]S(C(C)(C)C)=O)[CH:18]=[CH:19][C:20]=1[F:21]>C(OCC)C.O1CCCC1>[Br:14][C:15]1[CH:16]=[C:17]([C:22]2([C:2]3[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH3:10])[CH:3]=3)[C:30]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:36]([NH2:37])=[N:23]2)[CH:18]=[CH:19][C:20]=1[F:21]

Participants

7

Reactant 4

HCID 807IodineHCID 6083154-Bromo-1-methoxy-2-methylbenzeneHCID 5462224MagnesiumHCID 72335435HCID 72335435, compound

Product 1

HCID 59596235HCID 59596235, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromo-1-methoxy-2-methylbenzene (1.21 g, 6.0 mmol) in diethyl ether (10 mL) was added dropwise to magnesium (0.22 g, 9.0 mmol) and iodine. The resulting mixture was heated to reflux for 2 h and was then allowed to cool to room temperature. The prepared reagent was added to a solution of N-((3-bromo-4-fluorophenyl)(2-cyanophenyl)methylene)-2-methylpropane-2-sulfinamide (Scheme #11 F, 0.82 g, 2.0 mmol) in tetrahydrofuran (20 mL) at 0°. The mixture was stirred at 0° C. for 1 h and then quenched by addition of saturated aqueous ammonium chloride. The reaction mixture was partitioned between water and ethyl acetate, the organic phase was dried over magnesium sulfate and evaporated. The residue was dissolved in methanol (20 mL) and was treated with hydrochloric acid (2M in diethyl ether, 2 mL) overnight. The solvent was evaporated and the residue was partitioned between saturated aqueous sodium bicarbonate and chloroform, the organic phase was dried over magnesium sulfate and evaporated. Purification by flash chromatography using chloroform:methanol (9:1) afforded 0.53 g (63% yield) of the title compound. 1H NMR (DMSO-d6) δ 7.90-7.74 (m, 1 H), 7.74-7.67 (m, 1 H), 7.59-7.42 (m, 3 H), 7.35-7.21 (m, 2 H), 7.12-7.00 (m, 2 H), 6.97-6.71 (m, 3 H), 3.74 (s, 3 H), 2.06 (s, 3 H); MS (ESI) m/z 425, 427 [M+1]+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 h
  3. customquenched by addition of saturated aqueous ammonium chloride
  4. customThe reaction mixture was partitioned between water and ethyl acetate
  5. dry with materialthe organic phase was dried over magnesium sulfate
  6. customevaporated
  7. dissolutionThe residue was dissolved in methanol (20 mL)
  8. additionwas treated with hydrochloric acid (2M in diethyl ether, 2 mL) overnight
  9. customThe solvent was evaporated
  10. customthe residue was partitioned between saturated aqueous sodium bicarbonate and chloroform
  11. dry with materialthe organic phase was dried over magnesium sulfate
  12. customevaporated
  13. customPurification by flash chromatography

Sources & evidence

ORD record
ord-1e443399ca494540a84ff3e273b35f7e
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

Loading…