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1-Fluoro-2-iodobenzene → HCID 21099473、化合物

HRID 1351624
ノート
印刷プレビュー

反応式

HRID 1351624 の反応式
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])(=[O:11])=[O:10])=[CH:5][N:4]=1)=[CH2:2].[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1I.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)C.C(N(CC)CC)C.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1/[CH:2]=[CH:1]/[C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])(=[O:10])=[O:11])=[CH:5][N:4]=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 3

HCID 676731-Fluoro-2-iodobenzeneHCID 80271Tri-o-tolylphosphineHCID 21099480HCID 21099480、化合物

生成物 1

HCID 21099473HCID 21099473、化合物収率 57.4%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 8857Ethyl Acetate溶媒
HCID 21895542Acetonitrile triethylamine溶媒

反応条件

温度
170 °C

実験手順

2-Vinyl-5-[(2-fluorophenyl)sulfonyl]pyridine (Step 1, 50 mg, 0.19 mmol), 2-fluoroiodobenzene (46 mg, 0.207 mmol), palladium(II) acetate (2 mg, 0.01 mmol) and tri-o-tolylphosphine (12 mg, 0.039 mmol) were taken up in acetonitrile/triethylamine (0.5 mL/0.5 mL) and the reaction heated to 170° C. for 20 minutes in a Smith synthesiser microwave reactor. The reaction was diluted with ethyl acetate and washed with saturated aqueous ammonium chloride solution. The organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified by mass-triggered preparative HPLC (Nebula) to give the title compound as a beige solid (39 mg, 57%). δH (500 MHz, d6 DMSO): 9.03 (1H, d, J=2.2 Hz), 8.28 (1H, dd, J=1.6, 8.3 Hz), 8.05 (1H, td, J=7.6, 1.6 Hz), 7.92 (1H, d, J=16.1 Hz), 7.84 (1H, td, J=8.0, 1.4 Hz), 7.80–7.74 (2H, m), 7.47 (1H, d, J=16.1 Hz), 7.47 (1H, d, =0.7 Hz), 7.42–7.36 (2H, m), 7.27–7.21 (2H, m); m/z (ES+) 358 [MH+].

後処理

  1. washwashed with saturated aqueous ammonium chloride solution
  2. dry with materialThe organic layers were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by mass-triggered preparative HPLC (Nebula)

出典と根拠

ORDレコード
ord-afcb59ab87c34c418376728666ea16b1
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07217740B2

反応ノート

読み込み中…

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