Iodine → HCID 89964713, compound

HRID 1846221Notes

Reaction equation

HRID 1846221 reaction equation
[Mg].II.Br[C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1.[CH3:15][C:16]([S@@:19](/[N:21]=[C:22]1\[CH2:23][CH2:24][O:25][C:26]2[C:27]\1=[N:28][CH:29]=[CH:30][CH:31]=2)=[O:20])([CH3:18])[CH3:17]>CC1OCCC1>[CH3:18][C:16]([S@@:19]([NH:21][C@@:22]1([C:5]2[CH:14]=[CH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=2)[C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:26]2[O:25][CH2:24][CH2:23]1)=[O:20])([CH3:15])[CH3:17]

Participants

6

Reactant 4

HCID 807IodineHCID 113722-BromonaphthaleneHCID 5462224MagnesiumHCID 140633992HCID 140633992, compound

Product 1

HCID 89964713HCID 89964713, compound

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent3×

Procedure

To a solution of magnesium turnings (0.083 mL, 5.80 mmol) and iodine (10 mg) in 2-MeTHF (6 mL) under N2 at room temperature was slowly added a solution of 2-bromonaphthalene (1.0 g, 4.83 mmol) in 2-MeTHF (4 mL). After addition, the mixture was stirred at room temperature for 18 h. The mixture was cooled to −78° C., and a solution of (S,E)-2-methyl-N-(2H-pyrano[3,2-b]pyridin-4(3H)-ylidene)propane-2-sulfinamide (0.490 g, 1.942 mmol) in 2-MeTHF (3 mL) was added dropwise. The mixture was then stirred at −78° C. for 1 h and at room temperature for 5 h. The mixture was quenched with saturated NH4Cl (1.5 mL). The mixture was then extracted with EtOAc (2×5 mL). The combined organic extracts were dried over MgSO4, concentrated, and purified by silica gel column chromatography using ISCO (30-60% EtOAc/hexanes) to give the title compound as a yellow solid. MS (ESI, positive ion) m/z: 381.0 (M+H)

Workup

  1. additionAfter addition
  2. temperatureThe mixture was cooled to −78° C.
  3. stirringThe mixture was then stirred at −78° C. for 1 h and at room temperature for 5 h
  4. customThe mixture was quenched with saturated NH4Cl (1.5 mL)
  5. extractionThe mixture was then extracted with EtOAc (2×5 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-94c6df3764b84a0aaad857a1a5d7f249
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

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