Potassium Phosphate, Tribasic → 4-(3-Cyclopropyl-indole-1-sulfonyl)-N-(4-fluoro-benzyl)-benzamide

HRID 1178977ノート

反応式

HRID 1178977 の反応式
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8](=[O:28])[C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20](I)=[CH:19]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH:31]1(B(O)O)[CH2:33][CH2:32]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:31]1([C:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]([S:15]([C:12]3[CH:13]=[CH:14][C:9]([C:8]([NH:7][CH2:6][C:5]4[CH:29]=[CH:30][C:2]([F:1])=[CH:3][CH:4]=4)=[O:28])=[CH:10][CH:11]=3)(=[O:17])=[O:16])[CH:19]=2)[CH2:33][CH2:32]1

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 58975061N-(4-fluoro-benzyl)-4-(3-iodo-indole-1-sulfonyl)-benzamide

生成物 1

HCID 589750114-(3-Cyclopropyl-indole-1-sulfonyl)-N-(4-fluoro-benzyl)-benzamide収率 60%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

Combine N-(4-fluoro-benzyl)-4-(3-iodo-indole-1-sulfonyl)-benzamide (0.50 g, 0.94 mmol), cyclopropylboronic acid (0.24 g, 2.8 mmol), tricyclohexylphosphine (0.05 g, 0.18 mmol), potassium phosphate (0.70 g, 3.30 mmol), and palladium acetate (0.02 g, 0.09 mmol) in a mixture of toluene (15 mL) and water (0.4 mL). Heat to 100° C. under nitrogen for 18 hours, filter through celite, and wash solids with EtOAc. Wash EtOAc with saturated NaHCO3 (30 mL), then dry with Na2SO4, and concentrate under vacuum. Purify by flash column on silica gel eluting with 0-50% EtOAc in hexanes to give the title compound (0.25 g, 60%). MS (ES) 449.2 (M+1)+, 447.4 (M−1)−.

後処理

  1. filtrationfilter through celite
  2. washwash solids with EtOAc
  3. dry with materialWash EtOAc with saturated NaHCO3 (30 mL), then dry with Na2SO4
  4. concentrationconcentrate under vacuum
  5. customPurify by flash column on silica gel eluting with 0-50% EtOAc in hexanes

出典と根拠

ORDレコード
ord-f07dbabf5c5547138b6ced4349f08f3a
出典データセット
uspto-grants-2007_10
特許番号
US07276516B2

反応ノート

読み込み中…