Triethylamine → HCID 67479222, compound

HRID 472493Notes

Reaction equation

HRID 472493 reaction equation
[Cl:1][C:2]1[N:12]=[C:5]2[C:6]([CH:10]=[CH2:11])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]([CH3:25])[S:21]([CH3:24])(=[O:23])=[O:22].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[Cl:1][C:2]1[N:12]=[C:5]2[C:6](/[CH:10]=[CH:11]/[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:20]([CH3:25])[S:21]([CH3:24])(=[O:23])=[O:22])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 67478926N-(2-Bromophenyl)-N-methylmethanesulfonamideHCID 67481451HCID 67481451, compound

Product 1

HCID 67479222HCID 67479222, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

196 c) A tube was charged with 2-chloro-8-vinyl-[1,2,4]triazolo[1,5-a]pyridine (100.0 mg, 0.5568 mmol), N-(2-bromo-phenyl)-N-methyl-methanesulfonamide (140.0 mg, 0.5300 mmol), palladium acetate (4.0 mg, 0.018 mmol) and tri-o-tolylphosphine (26.0 mg, 0.0854 mmol), triethylamine (0.35 mL, 2.5 mmol) and acetonitrile (1 mL) under an atmosphere of nitrogen. The tube was sealed and the mixture was heated at 100° C. for 18 hours then cooled to room temperature, diluted with dichloromethane (30 mL) and washed with 2N Hydrochloric acid (10 mL). The organic layer was separated, dried over magnesium sulfate, filtered and evaporated. The residue was purified via chromatography (silica gel column 24 g and 10%→90% ethyl acetate:hexane). N-{2-[(E)-2-(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-vinyl]-phenyl}-N-methyl-methanesulfonamide was isolated as a tan foam (0.133 g, 69%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.52 (d, J=16.1 Hz, 1H), 8.40 (d, J=6.8 Hz, 1H), 7.86 (d, J=7.1 Hz, 1H), 7.65 (d, J=7.4 Hz, 1H), 7.46-7.30 (m, 3H), 7.20-7.05 (m, 2H), 3.36 (s, 3H), 3.19 (s, 3H). MS=363, 365 (MH)+.

Workup

  1. customThe tube was sealed
  2. temperaturethen cooled to room temperature
  3. washwashed with 2N Hydrochloric acid (10 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified via chromatography (silica gel column 24 g and 10%→90% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-f300cba091d641d496dfdd4dd2a291de
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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