Hydrochloric Acid → 6-Bromo-2',3',5',6'-tetrahydrospiro[indene-2,4'-pyran]-1(3H)-imine

HRID 539335Notes

Reaction equation

HRID 539335 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH2:13][C:7]1([CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)[C:6]2=[N:17]S(C(C)(C)C)=O.CCOCC>O1CCOCC1>[Br:2][C:3]1[CH:4]=[C:5]2[C:14]([CH2:13][C:7]3([C:6]2=[NH:17])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]3)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67979409N-(5-Bromo-2',3',5',6'-tetrahydrospiro[indene-2,4'-pyran]-3(1 H)-ylidene)-2-methylpropane-2-sulfinamide

Product 1

HCID 679795066-Bromo-2',3',5',6'-tetrahydrospiro[indene-2,4'-pyran]-1(3H)-imine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

HCl (4M in 1,4-dioxane) (0.683 mL, 2.73 mmol) was added to a solution of N-(5-bromo-2′,3′,5′,6′-tetrahydrospiro[indene-2,4′-pyran]-3(1H)-ylidene)-2-methylpropane-2-sulfinamide (Example 25 Step 1, 105 mg, 0.27 mmol) in anhydrous 1,4-dioxane (1 mL) and the resulting mixture was stirred under a nitrogen atmosphere at r.t. overnight. Et2O (3 mL) was added, the precipitate was filtered off, washed with Et2O and then dissolved in DCM (5 mL) and sat. aq. NaHCO3 (5 mL). The mixture was poured into a phase separator, the organic layer was collected and concentrated to give the title compound that was used in the next step without any further purification.

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with Et2O
  3. dissolutiondissolved in DCM (5 mL)
  4. additionThe mixture was poured into a phase separator
  5. customthe organic layer was collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-50c7c8cfa44344dfbdd46f535f5b8e16
Source dataset
uspto-grants-2014_10
Patent number
US08865911B2

Reaction notes

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