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Potassium Phosphate, Tribasic → (3,5-difluoro(4-pyridyl))-N-[5-(2,2-difluoro-6-methylbenzo[d]1,3-dioxolen-5-yl)(1,3-thiazol-2-yl)]carboxamide

HRID 1524248
ノート
印刷プレビュー

反応式

HRID 1524248 の反応式
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:17])[C:7]=1[C:8]([NH:10][C:11]1[S:12][C:13](Br)=[CH:14][N:15]=1)=[O:9].[F:18][C:19]1([F:38])[O:23][C:22]2[CH:24]=[C:25]([CH3:37])[C:26](B3OC(C)(C)C(C)(C)O3)=[CH:27][C:21]=2[O:20]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C.O1CCOCC1.O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:17])[C:7]=1[C:8]([NH:10][C:11]1[S:12][C:13]([C:26]2[C:25]([CH3:37])=[CH:24][C:22]3[O:23][C:19]([F:18])([F:38])[O:20][C:21]=3[CH:27]=2)=[CH:14][N:15]=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 3

HCID 62657Potassium Phosphate, TribasicHCID 584872352-(2,2-Difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 88576617(3,5-difluoro(4-pyridyl))-N-(5-bromo(1,3-thiazol-2-yl))carboxamide

生成物 1

HCID 56848403(3,5-difluoro(4-pyridyl))-N-[5-(2,2-difluoro-6-methylbenzo[d]1,3-dioxolen-5-yl)(1,3-thiazol-2-yl)]carboxamide収率 40.8%

試薬・触媒・溶媒 4

HCID 962
Water
溶媒
HCID 6342Acetonitrile溶媒
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

Argon was bubbled through a mixture of (3,5-difluoro(4-pyridyl))-N-(5-bromo(1,3-thiazol-2-yl))carboxamide (148) (32 mg, 0.1 mmol), 2-(2,2-difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (45 mg, 0.15 mmol), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (11 mg, 10% mol) and K3PO4 (32 mg) in 1 mL ACN, 1 mL dioxane, 0.5 ml H2O. The reaction mixture was heated at 85° C. for 4 h. After cooling to room temperature, the reaction mixture was taken up in ethyl acetate, washed with aqueous NaHCO3 and brine. The organic phase was dried (Na2SO4), concentrated and then subjected to prep HPLC chromatography to give (3,5-difluoro(4-pyridyl))-N-[5-(2,2-difluoro-6-methylbenzo[d]1,3-dioxolen-5-yl)(1,3-thiazol-2-yl)]carboxamide (149) (16.8 mg, yield: 40.8%, purity>95%). LC-MS: calcd. for C17H9F4N3O3S: 412 (M+1).

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed with aqueous NaHCO3 and brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-0edfcf7ded654216b46f6dd2bdb09151
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09079891B2

反応ノート

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