Sodium Carbonate → HCID 178514711, compound

HRID 1433198Notes

Reaction equation

HRID 1433198 reaction equation
Br[C:2]1[CH:22]=[CH:21][C:5]2[NH:6][C:7]([CH2:9][O:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)=[N:8][C:4]=2[CH:3]=1.C([NH:27][S:28]([C:31]1[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][C:32]=1B1OC(C)(C)C(C)(C)O1)(=[O:30])=[O:29])(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[F:40][C:37]([F:38])([F:39])[C:34]1[CH:33]=[CH:32][C:31]([S:28]([NH2:27])(=[O:29])=[O:30])=[C:36]([C:2]2[CH:22]=[CH:21][C:5]3[NH:6][C:7]([CH2:9][O:10][C:11]4[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=4)=[N:8][C:4]=3[CH:3]=2)[CH:35]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 69079408HCID 69079408, compoundHCID 178506219HCID 178506219, compound

Product 1

HCID 178514711HCID 178514711, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazole (0.100 g, 0.269 mmol, from Example 1.1), N-tert-butyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-4-trifluoromethyl-benzenesulfonamide (0.165 g, 0.404 mmol), sodium carbonate (0.171 g, 1.61 mmol), and 1,1′-[bis(di-tert-butylphosphino)ferrocene]-palladium dichloride (0.035 g, 0.0538 mmol) in DME (2 mL) and H2O (0.5 mL) was heated at 80° 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 as a off-white solid. The obtained material was dissolved in TFA (2 mL) and the resulting solution was heated to 60° C. for 3 hours. The reaction mixture was concentrated in vacuo to provide a residue which was purified by chromatography (silica, hexanes: EtOAc, 1:1) to afford the title compound as a brown solid (0.101 g, 73%). 1H NMR (400 MHz, CD3OD) δ (ppm): 0.33 (d, 1H, J=8.0 Hz), 7.89 (dd, 1H, J=8.0 Hz, J=1.2 Hz), 7.82 (d, 1H, J=0.8 Hz), 7.76 (d, 1H, J=8.8 Hz), 7.69-7.65 (m, 3H), 7.50 (dd, 1H, J=8.8 Hz, J=1.6 Hz), 7.28 (d, 2H, J=8.8 Hz), 5.62 (s, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C22H16F6N3O3S: 516.4 (M+H), Found 516.3.

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)

Sources & evidence

ORD record
ord-5904e1bb5bfa44a084d268953b2529b9
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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