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

HRID 716622ノート

反応式

HRID 716622 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-295d2d36d9954102b79748799afa703b
出典データセット
uspto-grants-2015_11
特許番号
US09192603B2

反応ノート

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