2-Bromopropene → 2-(2-propenyl)indole

HRID 1661361ノート

反応式

HRID 1661361 の反応式
[SnH3][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:11]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:16]=CC=C[CH:12]=1.[Li+].[Cl-].BrC(C)=C>CN(C=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:16]([C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:11]=[CH2:12]

参加物

7

反応物 4

HCID 112022-BromopropeneHCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 129655202HCID 129655202、化合物

生成物 1

HCID 100121502-(2-propenyl)indole

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

The 2-stannylindole 23-1 (1.280 g, 2.34 mmol; prepared using methods described in WO 03/010141), triphenylphosphine (0.065 g, 0.25 mmol), Cul (0.045 g, 0.24 mmol), LiCl (0.200 g, 4.72 mmol) and 2-bromopropene (0.444 mL, 5.00 mmol) were dissolved in DMF (6 mL) and the suspension degassed by bubbling Ar for 20 min. Pd2(dba)3 (0.035 g, 0.034 mmol) was added and after degassing for an additional 10 min, the reaction mixture was heated to 100° C. overnight. The suspension was then diluted with TBME (100 mL) and washed with brine (2×25 mL). The extract was dried (MgSO4) and concentrated under reduced pressure to give a residue that was purified by flash chromatography using 5-10% EtOAc in hexane as eluent. The desired 2-(2-propenyl)indole 23-2 was obtained as beige solid (0.57 g, 81% yield): MS-ES m/z 298.1 (MH+). The methyl ester 23-2 was saponified in the usual way (NaOH/DMSO) to give the corresponding carboxylic acid 23-3 in 96% yield: MS-ES m/z 284.1 (MH+).

後処理

  1. customthe suspension degassed
  2. customby bubbling Ar for 20 min
  3. customafter degassing for an additional 10 min
  4. additionThe suspension was then diluted with TBME (100 mL)
  5. washwashed with brine (2×25 mL)
  6. dry with materialThe extract was dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue that
  9. customwas purified by flash chromatography

出典と根拠

ORDレコード
ord-1097d2ec966f491b81bb862a66643755
出典データセット
uspto-grants-2011_10
特許番号
US08030309B2

反応ノート

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