Pyridine → 1-(6-Bromo-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]-1-yl)ethanone

HRID 1618499Notes

Reaction equation

HRID 1618499 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]2[NH:8][CH2:9][C:10]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:7]=[C:6]2[N:8]([C:22](=[O:24])[CH3:23])[CH2:9][C:10]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 582218836-Bromo-1,2-dihydrospiro(indole-3,4'-oxane)

Product 1

HCID 672853631-(6-Bromo-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
85 °C

Procedure

6-Bromo-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran] (2.53 g, 9.44 mmol) was dissolved in pyridine (8.39 mL, 104 mmol) and acetic anhydride (1.34 mL, 14.2 mmol) was added followed by DMAP (0.0576 g, 0.472 mmol). The reaction was heated to 85° C. for 90 min. After this time the reaction was concentrated in vacuo and the resulting oil was partitioned between EtOAc and 0.5N HCl. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by column chromatography to give 1-(6-bromo-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]-1-yl)ethanone.

Workup

  1. concentrationAfter this time the reaction was concentrated in vacuo
  2. customthe resulting oil was partitioned between EtOAc and 0.5N HCl
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-3f7aee9c982f4324b68eb03befddf701
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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