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1-Fluoro-2-iodobenzene → HCID 21099473, 화합물

HRID 2376939
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HRID 2376939 반응식
[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
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참가 물질

7

반응물 3

HCID 676731-Fluoro-2-iodobenzeneHCID 80271Tri-o-tolylphosphineHCID 21099480HCID 21099480, 화합물

생성물 1

HCID 21099473HCID 21099473, 화합물수율 57.4%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 8857Ethyl Acetate
용매
HCID 21895542Acetonitrile triethylamine용매

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온도
170 °C

실험 절차

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, I=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+].

후처리

  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)

출처 및 근거

ORD 기록
ord-341ec42a8d344d80bd704c9b741c928a
출처 데이터셋
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07468393B2

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