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Dimethylformamide → HCID 15512895、化合物

HRID 1386029
ノート
印刷プレビュー

反応式

HRID 1386029 の反応式
CN(C)[CH:3]=[O:4].[CH3:6][O:7][C:8]([C:10]1[N:11]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]([F:39])([F:38])[F:37])[S:12](=[O:29])(=[O:28])[C:13]2[CH:27]=[CH:26][CH:25]=[CH:24][C:14]=2[C:15]=1OS(C(F)(F)F)(=O)=O)=[O:9].C(=O)([O-])[O-].[K+].[K+].[CH3:46][O:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1B(O)O>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].C(OCC)C.C1(C)C=CC=CC=1>[CH3:6][O:7][C:8]([C:10]1[N:11]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]([F:38])([F:39])[F:37])[S:12](=[O:28])(=[O:29])[C:13]2[CH:27]=[CH:26][CH:25]=[CH:24][C:14]=2[C:15]=1[C:52]1[CH:53]=[C:48]([O:47][CH3:46])[CH:49]=[C:50]([O:4][CH3:3])[CH:51]=1)=[O:9]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 11124297HCID 11124297、化合物

生成物 1

HCID 15512895HCID 15512895、化合物収率 83%

試薬・触媒・溶媒 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
触媒
HCID 1140Toluene溶媒
HCID 3283Diethyl Ether溶媒

反応条件

温度
100 °C

実験手順

To dimethylformamide (18 mL) was added 1,1-dioxo-4-(trifluoromethanesulfonyloxy)-2-(2-trifluoromethyl-phenyl)-1,2-dihydro-1λ6-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester, (1.60 g, 3.0 mmol), palladium tetrakis(triphenyl phosphine) (0.2 g, 0.17 mmol), potassium carbonate (0.7 g. 6.0 mmol), 2-methoxy-phenyl-boronic acid (0.88 g, 6.0 mmol), and toluene (50 mL). The mixture was heated to 100° C. for 30 minutes and was filtered through a pad of Celite. The filtrate and EtOAc washing solution was washed three times with saturated sodium bicarbonate solution, brine, and dried over charcoal and anhydrous magnesium sulfate. The suspension was filtered and stripped to an oil which was resuspended in ethyl acetate and ethyl ether. Insoluble material from this mixture was filtered off, and the filtrate was concentrated in vacuo to an oil. The residue was chromatographed on silica gel eluted with a mixture of ethyl acetate and hexane (25:75). The appropriate fractions were concentrated in vacuo and crystallized from ethyl ether giving a solid 1.29 g, 83% yield.

後処理

  1. filtrationwas filtered through a pad of Celite
  2. washThe filtrate and EtOAc washing solution was washed three times with saturated sodium bicarbonate solution, brine
  3. dry with materialdried over charcoal and anhydrous magnesium sulfate
  4. filtrationThe suspension was filtered
  5. filtrationInsoluble material from this mixture was filtered off
  6. concentrationthe filtrate was concentrated in vacuo to an oil
  7. customThe residue was chromatographed on silica gel
  8. washeluted with a mixture of ethyl acetate and hexane (25:75)
  9. concentrationThe appropriate fractions were concentrated in vacuo

出典と根拠

ORDレコード
ord-b99f54c6b73a43dd8cacfc27e12c41d1
出典データセット
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06265399B1

反応ノート

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