Diisopropylethylamine → N-(5-((2-Chlorobenzyl)thio)-4-(trifluoromethyl)thiazol-2-yl)picolinamide

HRID 716622노트

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HRID 716622 반응식
Br[C:2]1[S:6][C:5]([NH:7][C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:4][C:3]=1[C:16]([F:19])([F:18])[F:17].C(N(C(C)C)CC)(C)C.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.[Cl:71][C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][C:73]=1[CH2:78][SH:79]>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].O1CCOCC1>[Cl:71][C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][C:73]=1[CH2:78][S:79][C:2]1[S:6][C:5]([NH:7][C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[N:4][C:3]=1[C:16]([F:19])([F:18])[F:17]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 5807592-Chlorobenzyl mercaptanHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86688229N-(5-Bromo-4-(trifluoromethyl)thiazol-2-yl)picolinamide

생성물 1

HCID 86688230N-(5-((2-Chlorobenzyl)thio)-4-(trifluoromethyl)thiazol-2-yl)picolinamide

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

In a 5 mL microwave vial was charged with N-(5-bromo-4-(trifluoromethyl)thiazol-2-yl)picolinamide (0.06 g, 0.2 mmol), diisopropylethylamine (59 μL, 0.34 mmol), Pd2(dba)3 (0.0048 g, 0.0085 mmol), Xantphos (0.0099 g, 0.017 mmol), 1,4-dioxane (0.6 mL) and 2-chlorophenylmethanethiol (22 μL, 0.17 mmol). The reaction mixture was purged with argon for 5 min; the vial was capped and heated at 100° C. for 15 h. the reaction mixture was cooled to room temperature, diluted with ethyl acetate (5 mL), filtered, washing with ethyl acetate (10 mL) and the filtrate was concentrated under vacuum. The residue was purified by column chromatography eluting with ethyl acetate/hexanes 0 to 30% to give the product.

후처리

  1. customThe reaction mixture was purged with argon for 5 min
  2. customthe vial was capped
  3. temperaturewas cooled to room temperature
  4. additiondiluted with ethyl acetate (5 mL)
  5. filtrationfiltered
  6. washwashing with ethyl acetate (10 mL)
  7. concentrationthe filtrate was concentrated under vacuum
  8. customThe residue was purified by column chromatography
  9. washeluting with ethyl acetate/hexanes 0 to 30%
  10. customto give the product

출처 및 근거

ORD 기록
ord-295d2d36d9954102b79748799afa703b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09192603B2

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