Diisopropylethylamine → 4-[3-(2,4-Dichloro-quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

HRID 2075673ノート

反応式

HRID 2075673 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][C:6](I)=[CH:7][CH:8]=2)[N:3]=1.[SH:14][C:15]1[CH:16]=[C:17]([C:21]2([C:27]#[N:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:18]=[CH:19][CH:20]=1.CCN(C(C)C)C(C)C.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]2[C:4](=[CH:5][C:6]([S:14][C:15]3[CH:16]=[C:17]([C:21]4([C:27]#[N:28])[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[CH:18]=[CH:19][CH:20]=3)=[CH:7][CH:8]=2)[N:3]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 187863864-(3-Mercapto-phenyl)-tetrahydro-pyran-4-carbonitrileHCID 866138212,4-Dichloro-7-iodo-quinoline

生成物 1

HCID 866138254-[3-(2,4-Dichloro-quinolin-7-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

2,4-Dichloro-7-iodo-quinoline (3.4 g, 10.5 mmol), 4-(3-mercapto-phenyl)-tetrahydro-pyran-4-carbonitrile (3a, 2.3 g, 10.5 mmol), iPr2NEt (3.67 mL, 21.0 mmol), Pd2dba3 (240 mg, 0.26 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (303 mg, 0.52 mmol) were dissolved in 1,4-dioxane (50 mL) and degassed for 10 minutes with N2. The reaction was then sealed and heated to 60° C. for 1 hour. After cooling to room temperature, the reaction was diluted with EtOAc and saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentration. The residue was purified by silica gel chromatography (30% EtOAc in hexanes) to give the desired product, 3b.

後処理

  1. customdegassed for 10 minutes with N2
  2. customThe reaction was then sealed
  3. temperatureAfter cooling to room temperature
  4. additionthe reaction was diluted with EtOAc and saturated aqueous NH4Cl
  5. extractionThe aqueous layer was extracted with EtOAc
  6. dry with materialthe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentration
  9. customThe residue was purified by silica gel chromatography (30% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-f7cf6a8aff294b7da929f79cd5125135
出典データセット
uspto-grants-2011_04
特許番号
US07919621B2

反応ノート

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