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1,2-Dimethoxyethane → 1-[3-(5-Fluoropyridin-3-yl)phenyl]-1-pyridin-4-yl-1H-isoindol-3-amine

HRID 2264729
ノート
印刷プレビュー

反応式

HRID 2264729 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH2:17])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[F:24][C:25]1[CH:26]=[N:27][CH:28]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:30]=1.C(=O)([O-])[O-].[K+].[K+].C(COC)OC>C(O)C.O>[F:24][C:25]1[CH:30]=[C:29]([C:2]2[CH:3]=[C:4]([C:8]3([C:18]4[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=4)[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:10]([NH2:17])=[N:9]3)[CH:5]=[CH:6][CH:7]=2)[CH:28]=[N:27][CH:26]=1
参加物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 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 164142683-Fluoro-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 595962471-(3-Bromophenyl)-1-pyridin-4-yl-1H-isoindol-3-amine

生成物 1

HCID 595962541-[3-(5-Fluoropyridin-3-yl)phenyl]-1-pyridin-4-yl-1H-isoindol-3-amine収率 54%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒
HCID 962Water溶媒

実験手順

A mixture of 1-(3-bromophenyl)-1-pyridin-4-yl-1H-isoindol-3-amine (Scheme #9, C) (0.073 g, 0.20 mmol), 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.067 g, 0.30 mmol), potassium carbonate (0.055 g, 0.40 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane adduct (0.020 g, 0.025 mmol), dimethoxyethane (2 mL), water (1 mL) and ethanol (0.3 mL) under an argon atmosphere was irradiated in a microwave at 100° C. for 15 min. The reaction mixture was filtered and partitioned between water and ethyl acetate, the organic phase was concentrated and the residue was purified by preparative HPLC, which gave the title compound (0.041 g, 54%). 1H NMR (DMSO-d6) δ 8.67-8.63 (m, 1 H), 8.57 (d, J=2.78 Hz, 1 H), 8.49-8.42 (m, 2 H), 7.99-7.90 (m, 2 H), 7.85-7.79 (m, 1 H), 7.67-7.62 (m, 2 H), 7.55-7.41 (m, 4 H), 7.37-7.28 (m, 2 H), 6.95 (br s, 2 H), 1.91 (s, 2.2 H); MS (ESI) m/z 381 [M+1]+.

後処理

  1. customwas irradiated in a microwave at 100° C. for 15 min
  2. filtrationThe reaction mixture was filtered
  3. custompartitioned between water and ethyl acetate
  4. concentrationthe organic phase was concentrated
  5. customthe residue was purified by preparative HPLC, which

出典と根拠

ORDレコード
ord-9b2e74a7eee94740ad0d05f2ca96fd20
出典データセット
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07855213B2

反応ノート

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