Potassium Carbonate → Spiro[cyclohexane-1,3'-indolin]-2'-one

HRID 990654Notes

Reaction equation

HRID 990654 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]12[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C(C1C=C(B(O)O)C=CC=1)=O.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:7]1[C:8]2[C:4](=[CH:3][CH:2]=[CH:10][CH:9]=2)[C:5]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:6]1=[O:11]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343563-Formylphenylboronic acidHCID 114714965'-Bromo-1',2'-dihydrospiro[cyclohexane-1,3'-indole]-2'-one

Product 1

HCID 12888301Spiro[cyclohexane-1,3'-indolin]-2'-oneYield 60.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 5′-bromospiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one (1.00 g, 3.57 mmol) in dimethoxyethane (20 cm3) was added tetrakis(triphenylphosphine)palladium (0.20 g, 0.17 mmol) under nitrogen. After 15 min. 3-formylphenylboronic acid (1.00 g, 6.93 g) was added followed by potassium carbonate (2.90 g, 21 mmol) in water (10 cm3). After 20 h at reflux, the mixture was cooled poured into water and extracted with EtOAc (×3). The combined organic extract was washed with sat. brine, dried (MgSO4) and evaporated. The residue was purified by column chromatography (SiO2, EtOAc: hexane, gradient elution) to afford the title compound (0.66 g, 2.15 mmol, 60%) as a white solid, 1H NMR (CDCl3) δ 1.65-1.85 (m, 6H), 1.86-2.08 (m, 4H), 7.22 (d, 1H, J=8 Hz), 7.48 (dd, 1Hz), J=8, 2 Hz), 7.61 (t, 1H, J=8 Hz), 7.66 (d, 1H, J=2 Hz), 7.81-7.88 (m, 2H), 8.06 (t, 1H, J=2 Hz), 8.30 (s, 1H, br); MS ((+)ESI) m/z 306 (M+H)+.

Workup

  1. temperatureAfter 20 h at reflux
  2. temperaturethe mixture was cooled
  3. extractionextracted with EtOAc (×3)
  4. extractionThe combined organic extract
  5. washwas washed with sat. brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by column chromatography (SiO2, EtOAc: hexane, gradient elution)

Sources & evidence

ORD record
ord-262e6018ff4d4ae7bd89dff280ae6e0c
Source dataset
uspto-grants-2002_10
Patent number
US06462032B1

Reaction notes

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