Toluene → Tert-butyl 5-(3-fluorophenyl)picolinate

HRID 711242노트

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HRID 711242 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[N:6][CH:7]=1.[F:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[F:15][C:16]1[CH:21]=[C:20]([C:2]2[CH:3]=[CH:4][C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[N:6][CH:7]=2)[CH:19]=[CH:18][CH:17]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 24997839tert-Butyl 5-bromopyridine-2-carboxylate

생성물 1

HCID 67208627Tert-butyl 5-(3-fluorophenyl)picolinate

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매

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온도
90 °C

실험 절차

To a reaction flask was added tert-butyl 5-bromopicolinate 33-4 (516 mg, 2.00 mmol), 3-fluorophenylboronic acid 6-6 (280 mg, 2.00 mmol), Pd(PPh3)4 (140 mg, 0.20 mmol), toluene (10 mL), ethanol (2 mL) and 2M Na2CO3 (3 mL). The reaction mixture was bubbled with nitrogen for 2 minutes and stirred at 90° C. for 10 hours with the flask sealed. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (100 mL) and washed with saturated NaHCO3 aqueous solution, H2O and brine. The organic phase was dried over Na2SO4 and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, and eluted with 30% hexanes in ethyl acetate to give tert-butyl 5-(3-fluorophenyl)picolinate 33-5 as a white solid. MS m/z 274.1 (M+1).

후처리

  1. customThe reaction mixture was bubbled with nitrogen for 2 minutes
  2. customsealed
  3. temperatureAfter cooling to room temperature
  4. additionthe reaction mixture was diluted with ethyl acetate (100 mL)
  5. washwashed with saturated NaHCO3 aqueous solution, H2O and brine
  6. dry with materialThe organic phase was dried over Na2SO4
  7. concentrationconcentrated to dryness by rotary evaporation
  8. customThe crude product was purified by silica gel flash chromatography
  9. washeluted with 30% hexanes in ethyl acetate

출처 및 근거

ORD 기록
ord-b7575e6a2afd41e2b9fe986ac056e729
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181235B2

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