Sodium Carbonate → HCID 67228130, compound

HRID 1515605Notes

Reaction equation

HRID 1515605 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([CH:19]4[CH2:23][O:22][C:21]([CH3:25])([CH3:24])[O:20]4)[CH:18]=[C:13]3[CH:12]=[C:11]2[C:26](OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:27][CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:44][S:45]([C:48]1[CH:53]=[CH:52][C:51](B(O)O)=[CH:50][CH:49]=1)(=[O:47])=[O:46].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([CH:19]4[CH2:23][O:22][C:21]([CH3:25])([CH3:24])[O:20]4)[CH:18]=[C:13]3[CH:12]=[C:11]2[C:26]([C:51]2[CH:52]=[CH:53][C:48]([S:45]([CH3:44])(=[O:47])=[O:46])=[CH:49][CH:50]=2)=[CH:27][CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 86654498HCID 86654498, compound

Product 1

HCID 67228130HCID 67228130, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of toluene-4-sulfonic acid 1-[1-benzenesulfonyl-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-2-cyclopentyl-vinyl ester (620 mg, 1 mmol), bis(triphenylphosphine)palladium(II) chloride (70.1 mg, 0.1 mmol) and 4-(methanesulfonyl)phenylboronic acid (460 mg, 2.3 mmol) in dioxane (6 mL) was added a 2M sodium carbonate solution (1.5 mL) at 25° C. The mixture was subjected to microwave irradiation for 1.5 h at 100° C. The mixture was cooled to 25° C., extracted with ethyl acetate, washed with brine and dried over anhydrous sodium sulfate. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 30% ethyl acetate/hexanes) afforded 1-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-1H-pyrrolo[2,3-b]pyridine (510 mg, 85%) as a light yellow solid: LC/MS m/e calcd for C32H35N2S2O6 [M+H]+ 607.77, observed 607.3; 1H NMR (400 MHz, CDCl3) δ ppm 1.47-1.62 (m, 4H), 1.52 (s, 3H), 1.60 (s, 3H), 1.71-1.98 (m, 4H), 2.68 (m, 1H), 3.07 (s, 3H), 3.80 (m, 1H), 4.40 (dd, J=6.3 Hz, 8.3 Hz, 1H), 5.22 (m, 1H), 6.35 (d, J=10.1 Hz, 1H), 6.58 (s, 1H), 7.29 (m, 2H), 7.37, 7.39 (2d, J=8.6 Hz, 2H), 7.49 (t, J=7.5 Hz, 1H), 7.74 (m, 2H), 7.78, 7.79 (2d, J=8.6 Hz, 2H), 7.96, 7.97 (2d, J=2.1 Hz, 1H), 8.50, 8.51 (2d, J=2.1 Hz, 1H).

Workup

  1. customirradiation for 1.5 h at 100° C
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-77f017df13ec4040922361e6e85a5c68
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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