Methyl p-toluenesulfonate → 5-Bromo-3-methoxy-3-prop-1-ynyl-1,3-dihydroindol-2-one

HRID 396235Notes

Reaction equation

HRID 396235 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([OH:15])[C:12]#[C:13][CH3:14].[CH3:16]C(C)([O-])C.[K+].C1(C)C=CC(S(OC)(=O)=O)=CC=1.[Cl-].[NH4+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([O:15][CH3:16])[C:12]#[C:13][CH3:14]

Participants

6

Reactant 4

HCID 6645Methyl p-toluenesulfonateHCID 25517Ammonium ChlorideHCID 120859385-Bromo-3-hydroxy-3-prop-1-ynyl-1,3-dihydroindol-2-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 120859375-Bromo-3-methoxy-3-prop-1-ynyl-1,3-dihydroindol-2-oneYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-3-hydroxy-3-prop-1-ynyl-1,3-dihydroindol-2-one (1.0 g, 3.75 mmol) in dry DMF (15 cm3) at 0° C., was added potassium tert-butoxide (1M in THF, 4.1 cm3, 4.1 mmol). After 15 min. methyl p-toluenesulfonate (0.85 g, 4.6 mmol) was added and the mixture was allowed to warm up to room temperature. After 16 h the mixture was poured into saturated ammonium chloride, extracted with EtOAc (×3), washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography (SiO2, EtOAc:hexane 1:3) to afford 5-bromo-3-methoxy-3-prop-1-ynyl-1,3-dihydroindol-2-one (0.62 g, 2.21 mmol, 59%): (CDCl3) δ inter alia 1.87 (s, 3H), 3.19 (s, 3H), 3.35 (s, 1H), 6.72 (d, 1H, J=8.3 Hz), 7.48 (dd, 1H, J=8.3, 2 Hz), 7.63 (d, 1H, J=2 Hz): MS (EI) m/z 279 (M)+.

Workup

  1. extractionextracted with EtOAc (×3)
  2. washwashed with water, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by column chromatography (SiO2, EtOAc:hexane 1:3)

Sources & evidence

ORD record
ord-d277c1c7857741eeb8280dbc268cb4fc
Source dataset
uspto-grants-2003_08
Patent number
US06608068B2

Reaction notes

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