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Ethyl Acetate → 1-(7-Fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile

HRID 1618532
ノート
印刷プレビュー

反応式

HRID 1618532 の反応式
Br[C:2]1[CH:3]=[C:4]2[N:10]([C:11]3[C:20]4[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=4)[N:14]=[C:13]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)[C:12]=3[CH3:28])[CH2:9][C:8]([CH3:30])([CH3:29])[C:5]2=[N:6][CH:7]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[C:65]([Sn](CCCC)(CCCC)CCCC)#[N:66].CCOC(C)=O>C1(C(N)C2CCCCC2)CCCCC1.CN1C(=O)CCC1.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].O>[F:21][C:17]1[CH:16]=[C:15]2[C:20]([C:11]([N:10]3[C:4]4[C:5](=[N:6][CH:7]=[C:2]([C:65]#[N:66])[CH:3]=4)[C:8]([CH3:30])([CH3:29])[CH2:9]3)=[C:12]([CH3:28])[C:13]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)=[N:14]2)=[CH:19][CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 8857Ethyl AcetateHCID 200512Stannanecarbonitrile, tributyl-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 672855904-(6-Bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline

生成物 1

HCID 672852091-(7-Fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒HCID 10774245alpha-Cyclohexylcyclohexanemethanamine溶媒

実験手順

A stirred solution of 4-(6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]-pyridin-1-yl)-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (95 mg, 0.20 mmol), Pd2dba3 (56 mg, 0.06 mmol), XPhos (58 mg, 0.6 mmol) and cyanotributyltin (65 mg, 0.20 mmol) in dicyclohexylmethylamine (1.5 mL) and NMP (1.0 mL) was heated in the microwave at 150° C. After this time the reaction was treated with EtOAc (100 mL) and water (50 mL). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo. Reverse phase HPLC (10% to 60% acetonitrile in water) gave 1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile. Mass Spectrum (ESI) m/e=410 (M+1).

後処理

  1. dry with materialThe separated organic layer was dried over MgSO4
  2. filtrationfiltered
  3. customevaporated in vacuo

出典と根拠

ORDレコード
ord-4e85132c1f9849a590790ad023002cd9
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08765940B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート