Hydrochloric Acid → HCID 22065094, compound

HRID 497540Notes

Reaction equation

HRID 497540 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=1[C:23]1[N:27]=[C:26]([C:28]2[C:32]([CH3:33])=[C:31](Br)[S:30][CH:29]=2)[N:25]([CH3:35])[N:24]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Cl>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.O.C(#N)C>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=1[C:23]1[N:27]=[C:26]([C:28]2[C:32]([CH3:33])=[C:31]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:14])([F:13])[F:1])=[CH:5][CH:6]=3)[S:30][CH:29]=2)[N:25]([CH3:35])[N:24]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 80271Tri-o-tolylphosphineHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 22065144HCID 22065144, compound

Product 1

HCID 22065094HCID 22065094, compoundYield 44.9%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-trifluoromethoxybenzeneboronic acid (0.4 g, 1.1 mmol), 3-(2-chloro-6-fluorophenyl)-5-[5-bromo-4-methylthien-3-yl]-1-methyl-1H-1,2,4-triazole (0.4 g, 1 mmol), sodium carbonate (0.2 g, 1.9 mmol), tri-o-tolylphosphine (32 mg, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (73 mg, 0.1 mmol) were refluxed under nitrogen for 16 hours in an acetonitrile (14 mL) and water (1.4 mL) solution. After cooling to room temperature, the reactants were poured into dilute hydrochloric acid (1 N, 50 mL) and extracted with ether (3×50 mL). The combined ethereal extracts were washed with water (100 mL), saturated aqueous bicarbonate (70 mL) and brine (50 mL), dried over magnesium sulphate, filtered and concentrated. The residue was chromatographed over silica to afford the product as a yellow gum (210 mg, 43%): 1H NMR (CDCl3) δ 7.55 (s, 1H), 7.49 (d, 2H), 7.28-7.39 (m, 4H), 7.11 (t, 1H), 4.03 (s, 3H), 2.33 (s, 3H); EI/MS 467 m/e (M−1).

Workup

  1. extractionextracted with ether (3×50 mL)
  2. washThe combined ethereal extracts were washed with water (100 mL), saturated aqueous bicarbonate (70 mL) and brine (50 mL)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed over silica

Sources & evidence

ORD record
ord-f35f3cb57b484c2ba1e4ebbddc9da3a0
Source dataset
uspto-grants-2005_09
Patent number
US06949576B2

Reaction notes

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