Cesium carbonate → N-(4-(benzylthio)-2-nitrophenyl)-4'-chloro-2-fluoro-5-methoxy-3'-methyl-[1,1'-biphenyl]-4-amine

HRID 1504386

반응식

HRID 1504386 반응식
[CH2:1]([S:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[C:30]([O:32][CH3:33])[C:29](I)=[CH:28][C:27]=2[F:35])=[CH:22][C:21]=1[CH3:36].COC1CCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[CH2:1]([S:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][C:29]2[C:30]([O:32][CH3:33])=[CH:31][C:26]([C:23]3[CH:24]=[CH:25][C:20]([Cl:19])=[C:21]([CH3:36])[CH:22]=3)=[C:27]([F:35])[CH:28]=2)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 138539Cyclopentyl methyl etherHCID 135509934-(Benzylthio)-2-nitroanilineHCID 1177369494'-Chloro-2-fluoro-4-iodo-5-methoxy-3'-methyl-1,1'-biphenyl

생성물 1

HCID 117737265N-(4-(benzylthio)-2-nitrophenyl)-4'-chloro-2-fluoro-5-methoxy-3'-methyl-[1,1'-biphenyl]-4-amine수율 72.8%

시약·촉매·용매 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

A RBF was charged with 4-(benzylthio)-2-nitroaniline (1.80 g, 6.91 mmol), 4′-chloro-2-fluoro-4-iodo-5-methoxy-3′-methyl-1,1′-biphenyl (2.86 g, 7.61 mmol), xantphos (0.200 g, 0.346 mmol), Pd2(dba)3 (0.158 g, 0.173 mmol), CPME (13.83 ml) and cesium carbonate (3.15 g, 9.68 mmol). A reflux condenser was attached and the flask was lowered into a 110° C. heating for 3 hours. The mixture was cooled to room temperature, diluted with EtOAc, and filtered through celite with the aid of EtOAc. The filtrate was concentrated. The oily residue was purified using Biotage and eluting with 0-50% EtOAc/Heptane to give N-(4-(benzylthio)-2-nitrophenyl)-4′-chloro-2-fluoro-5-methoxy-3′-methyl-[1,1′-biphenyl]-4-amine (2.56 g, 5.03 mmol, 72.7% yield) as a bright-yellow solid. m/z (ESI) 509.1 (M+H)+.

후처리

  1. customA reflux condenser was attached
  2. customwas lowered into a 110° C.
  3. temperatureheating for 3 hours
  4. filtrationfiltered through celite with the aid of EtOAc
  5. concentrationThe filtrate was concentrated
  6. customThe oily residue was purified
  7. washeluting with 0-50% EtOAc/Heptane

출처 및 근거

ORD 기록
ord-3d1ba1a0155f4a3591f6978a9be3688e
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212182B2

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