Tetrabutylammonium Fluoride → HCID 136492461, 화합물

HRID 508925노트

반응식

HRID 508925 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:10][C:11](=[O:22])[N:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[CH:21])=[CH:16][CH:15]=2)[N:13]=1.I[C:24]1[CH:25]=[CH:26][C:27]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[N:28][CH:29]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>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.CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:10][C:11](=[O:22])[N:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[C:21][C:24]3[CH:29]=[N:28][C:27]([N:30]4[CH2:31][CH2:32][O:33][CH2:34][CH2:35]4)=[CH:26][CH:25]=3)=[CH:16][CH:15]=2)[N:13]=1

참가 물질

6

반응물 3

HCID 2724141Tetrabutylammonium FluorideHCID 27953624-(5-Iodo-2-pyridyl)morpholineHCID 1366448585-(2-chloro-6-fluorophenyl)-2-(4-ethynylphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

생성물 1

HCID 136492461HCID 136492461, 화합물수율 13.2%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 679Dimethyl Sulfoxide용매

실험 절차

The title compound was prepared according to the procedure described in Example-3 using 5-(2-chloro-6-fluorophenyl)-2-(4-ethynylphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (Intermediate-2, 0.100 g, 0.319 mmol), 4-(5-iodopyridin-2-yl)morpholine (Intermediate-6, 0.139 g, 0.470 mmol), TBAF (0.201 g, 0.638 mmol), bis(triphenylphosphine)palladium(II) chloride (0.020 g, 0.028 mmol) and DMSO (3.0 mL). The obtained product was purified with column chromatography on silica gel eluting with 2.0% MeOH:DCM to afford 0.020 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 3.58-3.61 (m, 4H), 3.82-3.85 (br s, 4H), 6.64 (d, J=8.7 Hz, 1H), 7.19 (t, J=8.7 Hz, 1H), 7.36-7.47 (m, 2H), 7.58 (d, J=8.4 Hz, 2H), 7.63-7.67 (m, 1H), 8.03 (d, J=9.0 Hz, 2H), 8.38 (s, 1H), 10.14 (br s, 1H); MS (m/z): 473.64 (M−H)−.

후처리

  1. customThe title compound was prepared
  2. customThe obtained product was purified with column chromatography on silica gel eluting with 2.0% MeOH

출처 및 근거

ORD 기록
ord-32917fd86f354cb28257baf5272ae961
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096545B2

반응 노트

불러오는 중…