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1,4-Dioxane → 4-[(2,4-Dimethoxy-benzyl)-methyl-amino]-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

HRID 1644632
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HRID 1644632 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+].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.O1CCOCC1.[CH3:72][O:73][C:74]1[CH:82]=[C:81]([O:83][CH3:84])[CH:80]=[CH:79][C:75]=1[CH2:76][NH:77][CH3:78]>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]>[CH3:72][O:73][C:74]1[CH:82]=[C:81]([O:83][CH3:84])[CH:80]=[CH:79][C:75]=1[CH2:76][N:77]([CH3:78])[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 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 312751,4-DioxaneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 2416536[(2,4-Dimethoxyphenyl)methyl](methyl)amineHCID 23676156Sodium t-butoxideHCID 251383534-Bromo-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

생성물 1

HCID 57551197
4-[(2,4-Dimethoxy-benzyl)-methyl-amino]-2-fluoro-N-thiazol-2-yl-benzenesulfonamide

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

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온도
100 °C

실험 절차

Into a vial was added the [B] 4-bromo-2-fluoro-N-thiazol-2-yl-benzenesulfonamide (170 mg, 0.00050 mol), sodium tert-butoxide (117 mg, 0.00121 mol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (18 mg, 0.000030 mol), Tris(dibenzylideneacetone)dipalladium(0) (9.3 mg, 0.000010 mol) and 1,4-dioxane (1.58 mL, 0.0202 mol). Argon was bubbled for 15 minutes. Into the reaction was added the [2,4-dimethoxy-benzyl)-methyl-amine (110 mg, 0.00061 mol) 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 compound as a yellow solid that was used in the next step without purification.

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

출처 및 근거

ORD 기록
ord-a84de43490e343aa99edab0487d675f6
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08124610B2

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