1,4-Dioxane → 4-(2,4-Dimethoxy-benzylamino)-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

HRID 1644626노트

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HRID 1644626 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[C:4]([F:17])[CH:3]=1.CC(C)([O-])C.[Na+].O1CCOCC1.[CH3:30][O:31][C:32]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:33]=1[CH2:34][NH2:35]>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=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:30][O:31][C:32]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:33]=1[CH2:34][NH:35][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[S:13][CH:14]=[CH:15][N:16]=2)(=[O:10])=[O:9])=[C:4]([F:17])[CH:3]=1

참가 물질

7

반응물 4

HCID 312751,4-DioxaneHCID 5972502,4-DimethoxybenzylamineHCID 23676156Sodium t-butoxideHCID 251383534-Bromo-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

생성물 1

HCID 575512544-(2,4-Dimethoxy-benzylamino)-2-fluoro-N-thiazol-2-yl-benzenesulfonamide수율 79.3%

시약·촉매·용매 2

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

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온도
100 °C

실험 절차

Into a vial was added the 4-bromo-2-fluoro-N-thiazol-2-yl-benzenesulfonamide (2.60 g, 0.00771 mol), sodium tert-butoxide (1.78 g, 0.0185 mol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.27 g, 0.00046 mol), tris(dibenzylideneacetone)dipalladium(0) (0.14 g, 0.00015 mol) and 1,4-dioxane (24.1 mL, 0.308 mol). Argon was bubbled for 15 minutes. 2,4-Dimethoxybenzylamine (1.40 mL, 0.00925 mol) was added and the reaction mixture was heated at 100° C. overnight. The reaction mixture was cooled to room temperature then filtered over Celite. The filtrate was concentrated to give the crude product that was purified via automated flash chromatography (silica gel, 50% EtOAc in hexanes to 100% EtOAc) to give the product as a yellow solid (2.59 g, 79.3%).

후처리

  1. customArgon was bubbled for 15 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthen filtered over Celite
  4. concentrationThe filtrate was concentrated
  5. customto give the crude product that
  6. customwas purified

출처 및 근거

ORD 기록
ord-69d401905e0b470891e5df3d98f7a9b9
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124610B2

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