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Sodium Carbonate → HCID 90203384, 화합물

HRID 1480058
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HRID 1480058 반응식
Br[CH2:2][C:3]1[C:8]([Cl:9])=[CH:7][N:6]=[C:5]([Cl:10])[CH:4]=1.[F:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[Cl:10][C:5]1[CH:4]=[C:3]([CH2:2][C:15]2[CH:14]=[CH:13][C:12]([F:11])=[CH:17][CH:16]=2)[C:8]([Cl:9])=[CH:7][N:6]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 90203452HCID 90203452, 화합물

생성물 1

HCID 90203384HCID 90203384, 화합물수율 45.2%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

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온도
80 °C

실험 절차

To a solution of 4-bromomethyl-2,5-dichloro-pyridine (500 mg, 2.08 mmol) in toluene (10 mL) was added with stirring the [1,1-bis(diphenylphos-phino)ferrocene]dichloropalladium DCM complex (74 mg, 0.101 mmol), B-(3-fluorophenyl)-boronic acid (290 mg, 2.08 mmol) and sodium carbonate (440 mg, 4.15 mmol) in water (2 mL). The resulting mixture was stirred at 80° C. for 3 h, cooled, poured onto water (20 mL), and partitioned between water and ethyl acetate. The organic portions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (silica, heptane/ethyl acetate gradient) to give the title compound (241 mg, 32%) as white solid. LC-MS (UV peak area, m/z) 70%, 255.0, 257.0 (M+).

후처리

  1. temperaturecooled
  2. additionpoured onto water (20 mL)
  3. custompartitioned between water and ethyl acetate
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (silica, heptane/ethyl acetate gradient)

출처 및 근거

ORD 기록
ord-dbb0a73c2d5d42728d500c73632a13d0
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409866B2

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