Water → methyl 2-[2-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-1H-indol-3-yl]pentanoate

HRID 591000ノート

反応式

HRID 591000 の反応式
C(=O)([O-])[O-].[Na+].[Na+].O.CC1(C)C(C)(C)OB([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[O:22][CH2:21][CH2:20][CH2:19]3)O1.Br[C:28]1[N:29]([CH3:45])[C:30]2[C:35]([C:36]=1[CH:37]([CH2:42][CH2:43][CH3:44])[C:38]([O:40][CH3:41])=[O:39])=[CH:34][CH:33]=[CH:32][CH:31]=2>CN(C)C=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[O:22]1[C:23]2[CH:24]=[CH:25][C:16]([C:28]3[N:29]([CH3:45])[C:30]4[C:35]([C:36]=3[CH:37]([CH2:42][CH2:43][CH3:44])[C:38]([O:40][CH3:41])=[O:39])=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:17][C:18]=2[CH2:19][CH2:20][CH2:21]1

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 438110342-(3,4-dihydro-2H-1-benzopyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 70819053methyl 2-(2-bromo-1-methyl-1H-indol-3-yl)pentanoate

生成物 1

HCID 70855400methyl 2-[2-(3,4-dihydro-2H-1-benzopyran-6-yl)-1-methyl-1H-indol-3-yl]pentanoate収率 86%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

Under a nitrogen atmosphere, sodium carbonate (370 mg, 3.5 mmol), water (20 mL), palladium tetrakis(triphenylphosphine) (620 mg, 0.54 mmol) and 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (904 mg, 3.48 mmol) were added to a solution of methyl 2-(2-bromo-1-methyl-1H-indol-3-yl)pentanoate (1.13 g, 3.4 mmol) in N,N-dimethylformamide (80 mL). The mixture was heated at 110° C. for 2 hours, concentrated in vacuo and water (40 mL) was added. The aqueous layer was extracted with ethyl acetate (2×20 mL). The organic layer was washed with brine (20 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5) to afford the desired product (12d) as a white solid (1.1 g, 2.91 mmol, 86%).

後処理

  1. concentrationconcentrated in vacuo and water (40 mL)
  2. additionwas added
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
  4. washThe organic layer was washed with brine (20 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 95/5)

出典と根拠

ORDレコード
ord-8fb792da203b4b21b3270f8714fef202
出典データセット
uspto-grants-2016_01
特許番号
US09238026B2

反応ノート

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