2-Bromopropene → 2-(2-propenyl)indole

HRID 731125노트

반응식

HRID 731125 반응식
[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.[Cu]I.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]

참가 물질

8

반응물 4

HCID 112022-BromopropeneHCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 129655202HCID 129655202, 화합물

생성물 1

HCID 100121502-(2-propenyl)indole

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

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), CuI (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+).

후처리

  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

출처 및 근거

ORD 기록
ord-58c2ba25824c4a22aa3a6c5378bf095b
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582770B2

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