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

HRID 1264527

反応式

HRID 1264527 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6d240a5ee1474e68bab99f5023c43496
出典データセット
uspto-grants-2003_04
特許番号
US06544970B2

関連ノート

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