Triethylamine → HCID 67479222, 화합물

HRID 472493노트

반응식

HRID 472493 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 67479222HCID 67479222, 화합물

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-f300cba091d641d496dfdd4dd2a291de
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633173B2

반응 노트

불러오는 중…