Water → HCID 86698767、化合物

HRID 1054777ノート

反応式

HRID 1054777 の反応式
Br[C:2]1[CH:13]=[CH:12][C:5]2[O:6][C@H:7]([CH2:10][OH:11])[CH2:8][O:9][C:4]=2[CH:3]=1.[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([CH:19]=[CH:20][NH:21]2)=[CH:17][C:16]=1B1OCC(C)(C)CO1.[C:32](=O)([O-])[O-:33].[K+].[K+].O>CN(C=O)C.O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Cl:14][C:15]1[CH:23]=[C:22]2[C:18]([C:19]([CH:32]=[O:33])=[CH:20][NH:21]2)=[CH:17][C:16]=1[C:2]1[CH:13]=[CH:12][C:5]2[O:6][C@H:7]([CH2:10][OH:11])[CH2:8][O:9][C:4]=2[CH:3]=1

参加物

9

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 46942285[(2R)-6-Bromo-2,3-dihydro-1,4-benzodioxin-2-yl]methanolHCID 866987336-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole

生成物 1

HCID 86698767HCID 86698767、化合物収率 141.9%

試薬・触媒・溶媒 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of [(2R)-6-bromo-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (0.54 g, 2.05 mmol) (which can be prepared as in Biorg. Med. Chem. 2007, 15, 4048.), 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (0.52 g, 4.06 mmol) in DMF (4 mL) and dioxane (4 mL) was stirred at room temperature for 30 min. under N2. Pd(dppf)Cl2 (100 mg, 0.137 mmol) and 2 N potassium carbonate (10 mL, 20 mmol) was added. The resulting mixture was stirred for 30 min. at 90° C. under N2. TLC showed the reaction was complete. Water (50 mL) and methylene chloride (50 mL) was added. The aqueous layer was extracted with methylene chloride (30 mL×3). The combined organic layer was dried over sodium sulfate, filtered and evaporated to give the title compound (1 g) which was used in the next step without further purification.

後処理

  1. stirringThe resulting mixture was stirred for 30 min. at 90° C. under N2
  2. extractionThe aqueous layer was extracted with methylene chloride (30 mL×3)
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

出典と根拠

ORDレコード
ord-2e8fa3c00ff745cda30570598101ac54
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

反応ノート

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