Sodium Carbonate → HCID 21099406, compound

HRID 2376951Notes

Reaction equation

HRID 2376951 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]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>O.C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh]>[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[CH2:2][CH2:1][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

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343342,4-Difluorophenylboronic acidHCID 21099480HCID 21099480, compound

Product 1

HCID 21099406HCID 21099406, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 6436379Rhodium, di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)di-CatalystHCID 962WaterSolvent2×

Conditions

Temperature
150 °C

Procedure

2-Vinyl-5-[(2-fluorophenyl)sulfonyl]pyridine (Example 6 Step 1; 50 mg, 0.19 mmol), 2,4-difluorophenylboronic acid (75 mg, 0.475 mmol), chloro(1,5-cyclooctadiene)rhodium(I) dimer (2 mg, 0.004 mmol) and sodium carbonate (40 mg, 0.377 mmol) were taken up in water (1 mL) and heated in a microwave reactor at 150° C. for 10 minutes. The dark suspension was diluted with water and extracted with ethyl acetate (×2). The combined organic layers were washed with brine, dried over MgSO4 and concentrated while loading onto silica. Eluting through a plug of silica using 20% ethyl acetate/isohexane followed by mass-triggered preparative HPLC gave the title compound as a pale yellow solid (10 mg, 14%). δH (500 MHz, d6 DMSO): 8.99 (1H, s), 8.21 (1H, dd, J=1.8, 8.3 Hz), 8.06 (1H, td, J=1.6, 7.6 Hz), 7.84-7.78 (1H, m), 7.52-7.48 (2H, m), 7.43 (1H, t, J=9.5 Hz), 7.28 (1H, q, J=8.0 Hz), 7.11 (1H, td, J=2.4, 9.9 Hz), 6.94 (1H, td, J=2.1, 8.5 Hz), 3.12-3.10 (2H, m), 3.01-2.98 (2H, m); m/z (ES+) 378 [MH+].

Workup

  1. extractionextracted with ethyl acetate (×2)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. washEluting through a plug of silica using 20% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-52f4d58c7ea245a0b06afb6e43f1cb9a
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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