Sodium Carbonate → 5-(3,4-dihydro-2H-1-benzopyran-6-yl)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde

HRID 591049노트

반응식

HRID 591049 반응식
Cl[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[CH:9]=[O:10].C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[O:31][CH2:30][CH2:29][CH2:28]3)O1>C(COC)OC.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:31]1[C:32]2[CH:33]=[CH:34][C:25]([C:2]3[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=3[CH:9]=[O:10])=[CH:26][C:27]=2[CH2:28][CH2:29][CH2:30]1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 27773975-Chloro-1,3-dimethylpyrazole-4-carboxaldehydeHCID 438110342-(3,4-dihydro-2H-1-benzopyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 867178435-(3,4-dihydro-2H-1-benzopyran-6-yl)-1,3-dimethyl-1H-pyrazole-4-carbaldehyde수율 34.1%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

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온도
85 °C

실험 절차

A solution of 5-chloro-1,3-dimethyl-1H-pyrazole-4-carboxaldehyde (200 mg, 1.26 mmol), sodium carbonate (282 mg, 2.66 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman (426 mg, 1.64 mmol) and palladium tetrakis(triphenylphosphine) (73 mg, 0.063 mmol) in a mixture of dimethoxyethane (4 mL) and water (1.35 mL) was heated at 85° C. for 24 hours. After cooling to room temperature, the mixture was poured into water (10 mL). The aqueous layer was extracted with ethyl acetate (2×10 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20 then 50/50) to provide the desired product (27a) (110 mg, 0.43 mmol, 34%) as a beige solid.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20

출처 및 근거

ORD 기록
ord-9812fcb2319c47f0a3c7d309fdb338a6
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

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