Sodium Carbonate → HCID 71622394, compound

HRID 1505616Notes

Reaction equation

HRID 1505616 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:20][C:21]([F:24])([F:23])[F:22])[S:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[C:4]([F:25])[CH:3]=1.[N:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[F:25][C:4]1[CH:3]=[C:2]([C:29]2[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=2)[CH:7]=[CH:6][C:5]=1[CH2:8][N:9]([CH2:20][C:21]([F:24])([F:23])[F:22])[S:10]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:12])=[O:11]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 86690639HCID 86690639, compound

Product 1

HCID 71622394HCID 71622394, compoundYield 93%

Conditions

Temperature
80 °C

Procedure

N-[(4-bromo-2-fluoro-phenyl)methyl]-1-phenyl-N-(2,2,2-trifluoroethyl)methanesulfonamide (Example 2, Step 2) (2 g, 4.54 mmol), 4-pyridylboronic acid (931 mg, 6.81 mmol) dichlorobis(di-tert-butyl(4-dimethylaminophenyl)phosphine)palladium(II) (161 mg, 0.23 mmol) potassium acetate (669 mg, 6.81 mmol) and sodium carbonate (722 mg, 6.81 mmol) were combined and the reaction was purged with nitrogen. Acetonitrile (15 mL) and water (4.5 mL) were then added and the reaction was stirred at 80° C. for 16 hours. The reaction was filtered through diatomaceous earth, concentrated and purified by silica gel column chromatography (20-100% EtOAc in heptane) to give N-[[2-fluoro-4-(4-pyridyl)phenyl]methyl]-1-phenyl-N-(2,2,2-trifluoroethyl)methanesulfonamide (1.85 g, 93% yield). 1H NMR (400 MHz, DMSO) δ 8.69-8.62 (m, 2H), 7.79-7.74 (m, 2H), 7.74-7.66 (m, 2H), 7.57 (t, J=8.1 Hz, 1H), 7.50-7.36 (m, 5H), 4.68 (s, 2H), 4.53 (s, 2H), 4.04 (q, J=9.3 Hz, 2H); LCMS (m/z) ES+ 439.0 [M+1]+.

Workup

  1. customthe reaction was purged with nitrogen
  2. additionAcetonitrile (15 mL) and water (4.5 mL) were then added
  3. filtrationThe reaction was filtered through diatomaceous earth
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (20-100% EtOAc in heptane)

Sources & evidence

ORD record
ord-21208548fe1a4ee1a5e877c70960f908
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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