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Stannanecarbonitrile, tributyl- → 1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile

HRID 1618771
ノート
印刷プレビュー

反応式

HRID 1618771 の反応式
Br[C:2]1[N:7]=[C:6]2[C:8]([CH3:30])([CH3:29])[CH2:9][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])[C:5]2=[CH:4][C:3]=1[N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.C([Sn]([C:50]#[N:51])(CCCC)CCCC)CCC>CN1C(=O)CCC1.CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=C(C(C)C)C=1)C.C1C=[C-]C(CCN)=CC=1.Cl[Pd+]>[F:21][C:17]1[CH:16]=[C:15]2[C:20]([C:11]([N:10]3[C:5]4[C:6](=[N:7][C:2]([C:50]#[N:51])=[C:3]([N:31]5[CH2:32][CH2:33][O:34][CH2:35][CH2:36]5)[CH:4]=4)[C:8]([CH3:29])([CH3:30])[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 200512Stannanecarbonitrile, tributyl-HCID 866642814-(5-bromo-3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline

生成物 1

HCID 509394701-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile

試薬・触媒・溶媒 2

HCID 54751079XPhos Palladacycle
触媒
HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
140 °C

実験手順

To a stirred solution of 4-(5-bromo-3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridin-1-yl)-7-fluoro-3-methyl-2-(2-pyridinyl)quinoline (61 mg, 0.111 mmol) in NMP (1.5 mL) was added tri-n-butyltin cyanide (35.2 mg, 0.111 mmol), XPhos precatalyst (16.3 mg, 0.022 mmol) and heated at 140° C. for 2 h in the microwave. 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. Purification by reverse phase HPLC (10 to 60% acetonitrile water) gave 1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-3,3-dimethyl-6-(4-morpholinyl)-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile. 1H NMR (400 MHz, chloroform-d) δ ppm 8.68-8.80 (1H, m), 7.84-7.99 (3H, m), 7.67 (1H, dd, J=9.2, 5.9 Hz), 7.44 (1H, ddd, J=6.9, 4.9, 1.9 Hz), 7.35 (1H, ddd, J=9.2, 8.0, 2.5 Hz), 5.74 (1H, s), 3.87 (2H, s), 3.79 (4H, t, J=4.7 Hz), 2.94-3.11 (4H, m), 2.40 (3H, s), 1.59 (3H, s), 1.53 (3H, s). Mass Spectrum (ESI) m/e=495.0 (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
  5. customPurification by reverse phase HPLC (10 to 60% acetonitrile water)

出典と根拠

ORDレコード
ord-95710f8a862a42688d81c2ad1527ea20
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反応条件実験手順後処理出典と根拠反応ノート