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Potassium Phosphate, Tribasic → 4-(6-(3,6-dihydro-2H-pyran-4-yl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline

HRID 1618667
ノート
印刷プレビュー

反応式

HRID 1618667 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.[O:31]1[CH2:36][CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH2:33][CH2:32]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:31]1[CH2:32][CH:33]=[C:34]([C:2]2[CH:3]=[C:4]3[N:10]([C:11]4[C:20]5[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=5)[N:14]=[C:13]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=5)[C:12]=4[CH3:28])[CH2:9][C:8]([CH3:30])([CH3:29])[C:5]3=[N:6][CH:7]=2)[CH2:35][CH2:36]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 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 50939729
4-(6-(3,6-dihydro-2H-pyran-4-yl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

A mixture 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 (150 mg, 0.324 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (102 mg, 0.486 mmol), potassium phosphate tribasic (206 mg, 0.971 mmol), Pd(OAc)2 (72.7 mg, 0.324 mmol) and SPhos (26.6 mg, 0.065 mmol) in toluene (2.5 mL) was heated in the microwave for 1 h at 100° C. After this time the reaction was partitioned between EtOAc (60 mL) and water (30 mL). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo. Column chromatography (hexanes:EtOAc, 1:0 to 0:1 as eluent) gave 4-(6-(3,6-dihydro-2H-pyran-4-yl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline. 1H NMR (500 MHz, chloroform-d) δ ppm 8.71-8.77 (1H, m), 7.97 (1H, d, J=2.0 Hz), 7.83-7.94 (3H, m), 7.79 (1H, dd, J=9.3, 5.9 Hz), 7.41 (1H, ddd, J=7.3, 4.9, 1.5 Hz), 7.30 (1H, ddd, J=9.2, 8.1, 2.6 Hz), 6.20 (1H, d, J=1.7 Hz), 5.90-5.95 (1H, m), 4.18-4.27 (2H, m), 3.78-3.90 (4H, m), 2.29-2.44 (5H, m), 1.61 (3H, s), 1.55 (3H, s). Mass Spectrum (ESI) m/e=467.2 (M+1).

後処理

  1. customAfter this time the reaction was partitioned between EtOAc (60 mL) and water (30 mL)
  2. dry with materialThe separated organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo

出典と根拠

ORDレコード
ord-a5a0eb5b389f464fbb93f6ef1357ccb5
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

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート