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

HRID 1351624
Notes
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Reaction equation

HRID 1351624 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

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

Product 1

HCID 21099473HCID 21099473, compoundYield 57.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst
HCID 8857
Ethyl Acetate
Solvent
HCID 21895542Acetonitrile triethylamineSolvent

Conditions

Temperature
170 °C

Procedure

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+].

Workup

  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)

Sources & evidence

ORD record
ord-afcb59ab87c34c418376728666ea16b1
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07217740B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes