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

HRID 1936958

反応式

HRID 1936958 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) δ10.6 (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-a7e5369329d4483e9990ae719c6b1799
出典データセット
uspto-grants-2002_05
特許番号
US06391907B1

関連ノート

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