Lithium Chloride → 5-(4-Ethyl-5-(3-fluoro-4-(1,3-thiazol-4-yl)phenyl)-3-trifluoromethyl-1H-pyrazol-1-yl)-2-pyridinesulfonamide

HRID 394891ノート

反応式

HRID 394891 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[N:17][CH:18]=3)[N:11]=[C:10]([C:23]([F:26])([F:25])[F:24])[C:9]=2[CH2:27][CH3:28])=[CH:4][C:3]=1[F:29].C([Sn](CCCC)(CCCC)[C:35]1[N:36]=[CH:37][S:38][CH:39]=1)CCC.[Cl-].[Li+]>O1CCOCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:27]([C:9]1[C:10]([C:23]([F:26])([F:25])[F:24])=[N:11][N:12]([C:13]2[CH:14]=[CH:15][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[N:17][CH:18]=2)[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([C:35]2[N:36]=[CH:37][S:38][CH:39]=2)=[C:3]([F:29])[CH:4]=1)[CH3:28]

参加物

7

反応物 3

HCID 433294Lithium ChlorideHCID 27632584-(Tri-n-butylstannyl)thiazoleHCID 223137915-(5-(4-Bromo-3-fluorophenyl)-4-ethyl-3-trifluoromethyl-1H-pyrazol-1-yl)-2-pyridinesulfonamide

生成物 1

HCID 178121315-(4-Ethyl-5-(3-fluoro-4-(1,3-thiazol-4-yl)phenyl)-3-trifluoromethyl-1H-pyrazol-1-yl)-2-pyridinesulfonamide収率 77.1%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 5-(5-(4-bromo-3-fluorophenyl)-4-ethyl-3-trifluoromethyl-1H-pyrazol-1-yl)-2-pyridinesulfonamide (450 mg, 0.912 mmol), 4-tributylstannyl-1,3-thiazol (410 mg, 1.095 mmol), tetrakis(triphenylphosphine)palladium (105 mg, 0.091 mmol), lithium chloride (97 mg, 2.281 mmol) in 1,4-dioxane (11 ml) was stirred at reflux for 17 h. After cooling, the mixture was diluted with ethyl acetate, washed with water. The organic layer was dried (MgSO4) and concentrated. This was purified on silica gel eluting with ethyl acetate/hexane (1:3/1:2) to afford 350 mg (77.1%) of the titled compound as a yellow solid.

後処理

  1. temperatureat reflux for 17 h
  2. temperatureAfter cooling
  3. washwashed with water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customThis was purified on silica gel eluting with ethyl acetate/hexane (1:3/1:2)

出典と根拠

ORDレコード
ord-9a99fc05fb2f423f8f2046d0148a6afb
出典データセット
uspto-grants-2003_08
特許番号
US06603008B1

反応ノート

読み込み中…