Sodium Carbonate → HCID 178514702, compound

HRID 1433235Notes

Reaction equation

HRID 1433235 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]2[NH:6][C:7]([CH2:9][O:10][C:11]3[CH:16]=[CH:15][C:14]([CH:17]4[CH2:19][CH2:18]4)=[CH:13][CH:12]=3)=[N:8][C:4]=2[CH:3]=1.C([NH:26][S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O)(=[O:29])=[O:28])(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.FC(F)(F)C(O)=O>[CH:17]1([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH2:9][C:7]3[NH:6][C:5]4[CH:20]=[CH:21][C:2]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=5[S:27]([NH2:26])(=[O:29])=[O:28])=[CH:3][C:4]=4[N:8]=3)=[CH:12][CH:13]=2)[CH2:19][CH2:18]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 4997616Boronic acid, B-(2-(((1,1-dimethylethyl)amino)sulfonyl)phenyl)-HCID 178419329HCID 178419329, compound

Product 1

HCID 178514702HCID 178514702, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromo-2-(4-cyclopropyl-phenoxymethyl)-1H-benzoimidazole (0.030 g, 0.0874 mmol), 2-(tert-butylamino)sulfonylphenylboronic acid (0.029 g, 0.114 mmol), sodium carbonate (0.079 g, 0.524 mmol), and 1,1′-[bis(di-tert-butylphosphino)ferrocene]-palladium dichloride (0.006 g, 0.00874 mmol) in DME (2 mL) and H2O (0.5 mL) was heated at 90° C. for 12 hours. The reaction mixture was concentrated under reduced pressure to provide a residue, which was purified by chromatography (silica, hexanes:EtOAc, 1:1) to afford the product. It was then dissolved in trifluoroacetic acid (3 mL) and heated to 60° C. for 2 hours. The reaction mixture was concentrated and the residue was purified by chromatography (silica, hexanes: EtOAc, 1:2) to afford the title compound as a light brown solid. 1H NMR (400 MHz, CD3OD) δ (ppm): 8.14 (dd, 1H, J=8.0 Hz, J=1.2 Hz), 7.77 (s, 1H), 7.73 (d, 1H, J=9.2 Hz), 7.65 (td, 1H, J=8.2 Hz, J=1.6 Hz), 7.50 (td, 1H, J=8.4 Hz, J=1.6 Hz), 7.51 (dd, 1H, J=8.8 Hz, J=1.2 Hz), 7.41 (dd, 1H, J=6.0 Hz, J=1.2 Hz), 7.08-6.99 (m, 4H), 5.50 (s, 2H), 1.90-1.84 (m, 1H), 0.92-0.90 (m, 2H), 0.62-0.58 (m, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C23H22N3O3S: 420.5 (M+H), Found 420.4.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto provide a residue, which
  3. customwas purified by chromatography (silica, hexanes:EtOAc, 1:1)
  4. customto afford the product
  5. temperatureheated to 60° C. for 2 hours
  6. concentrationThe reaction mixture was concentrated
  7. customthe residue was purified by chromatography (silica, hexanes: EtOAc, 1:2)

Sources & evidence

ORD record
ord-bff80592cb9e4b61ac4118c64e41b9e9
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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