Sodium Carbonate → 5-(3,3-Dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)furan-2-carbonitrile

HRID 7017

반응식

HRID 7017 반응식
[C:1]([C:3]1[O:7][C:6](Br)=[CH:5][CH:4]=1)#[N:2].[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2([CH:21](B(O)O)CC[CH2:18]2)[C:10]1=[O:25].C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>COCCOC.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>[CH3:18][C:11]1([CH3:21])[C:12]2[C:17](=[CH:16][CH:15]=[C:14]([C:6]3[O:7][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[CH:13]=2)[NH:9][C:10]1=[O:25]

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 7086705-Bromofuran-2-carbonitrileHCID 21986244(spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one-5-yl)boronic acid

생성물 1

HCID 220193425-(3,3-Dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)furan-2-carbonitrile수율 53.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A solution of 5-cyano-2-bromofuran (0.5 g, 2.6 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.2 g) in ethylene glycol dimethyl ether (20 cm3) was stirred under N2 for 20 minutes. To this mixture was then added (spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one-5-yl) boronic acid (0.9 g, 3.9 mmol) and sodium carbonate (0.8 g, 7.8 mmol) in water (5 cm3). The solution was brought to reflux for 18 hours and then cooled to room temperature, poured into 2N NaOH and extracted with EtOAc (×3). The combined extracts were washed with water, brine, dried (MgSO4), and evaporated. The residue was purified by column chromatography (SiO2, EtOAc, hexane) to afford the title compound (0.35 g, 49%) as an off-white solid. mp: 193–194° C.; 1H NMR (DMSO-d6) δ 10.6 (s, 1H), 7.7 (d, 2H, J=3.3 Hz), 7.6 (dd, 1H, J=1.6, 6.6 Hz), 7.1 (d, 1H, J=3.8 Hz), 6.9 (d, 1H, J=8.1 Hz), 2.0–1.8 (m, 8H); MS [M−H]−=277.

후처리

  1. temperatureto reflux for 18 hours
  2. extractionextracted with EtOAc (×3)
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography (SiO2, EtOAc, hexane)

출처 및 근거

ORD 기록
ord-a9efd0e3ceac474680ddb105e57d88d7
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084168B2

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