3-Nitrophenylboronic Acid → HCID 68674767, compound

HRID 1936942Notes

Reaction equation

HRID 1936942 reaction equation
Br[CH:2]1[C:6]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]2=[O:15])[CH2:5][CH2:4][CH2:3]1.[N+:16]([C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)([O-:18])=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>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:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2([CH2:2][CH2:3][CH2:4][CH2:5]2)[C:7]1=[O:15].[N+:16]([C:19]1[CH:24]=[C:23]([C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:15])[C:6]23[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:22]=[CH:21][CH:20]=1)([O-:18])=[O:17]

Participants

7

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 219862275-Bromo-spiro [cyclopentane-1,3'-[3h]indol]-2'(1'h)-one

Product 1

HCID 68674767HCID 68674767, compoundYield 123.6%

Reagents, catalysts & solvents 3

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

Procedure

A solution of 5-bromo-spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one (0.3 g, 1.1 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.07 g, 0.06 mmol) in dimethoxyethane (8 cm3) was stirred under N2 for 20 min. To this mixture was then added 3-nitrophenylboronic acid (0.23 g, 1.4 mmol) and sodium carbonate (0.36 g, 3.4 mmol) in water (3 cm3). The solution was brought to reflux for 3 h then cooled to RT, poured into water and extracted with EtOAc (×3). The combined organic extracts were washed with water, brine, dried (MgSO4), and evaporated. The residue was purified by column chromatography (SiO2, ethyl acetate: hexane 1:3) to afford the title compound (0.21 g, 0.68 mmol, 62%) as a yellow solid: mp. 238-240 C.; 1H NMR (DMSO-d6) δ1.89-1.99 (m, 8H), 6.96 (d, J=8.1 Hz, 1H), 7.58 (dd, J=8.1, 1.8 Hz, 1H), 7.66 (d, J=1.8 Hz, 1H), 7.71 (dd, J=8.0, 8.0 Hz, 1H), 8.13 (dd, J=7.0, 1.0 Hz, 2H), 8.4 (d, J=1.8 Hz, 1H), 10.42 ( br s, 1H); 13C NMR (dioxane-d8) δ26.31, 38.13 (t), 53.85 (s), 108.9, 121.15, 121,33, 126.23, 129.38, 132.11 (d), 132.6, 138.32, 141.84, 142.74, 149.14, 182.68 (s); MS (EI) m/z 308 (M)+.

Workup

  1. temperatureto reflux for 3 h
  2. extractionextracted with EtOAc (×3)
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography (SiO2, ethyl acetate: hexane 1:3)

Sources & evidence

ORD record
ord-1f39cb5b94d3429998d5777e5c543571
Source dataset
uspto-grants-2002_05
Patent number
US06391907B1

Reaction notes

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