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Potassium Carbonate → 1-[2-chloro-5-(hydroxymethyl)phenyl]-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one

HRID 1867069
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HRID 1867069 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[N:10]1[C:15]([CH3:16])=[CH:14][C:13]([OH:17])=[CH:12][C:11]1=[O:18].[F:19][C:20]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:21]=1[CH2:22]Br.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C.C(#N)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[N:10]1[C:15]([CH3:16])=[CH:14][C:13]([O:17][CH2:22][C:21]2[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:20]=2[F:19])=[CH:12][C:11]1=[O:18]
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참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 516892Sodium BicarbonateHCID 547241841-[2-chloro-5-(hydroxymethyl)phenyl]-4-hydroxy-6-methylpyridin-2(1H)-one

생성물 1

HCID 220502741-[2-chloro-5-(hydroxymethyl)phenyl]-4-[(2,4-difluorobenzyl)oxy]-6-methylpyridin-2(1H)-one

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 18373917Acetonitrile--water (1/1)용매

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온도
0 °C

실험 절차

1-[2-chloro-5-(hydroxymethyl)phenyl]-4-hydroxy-6-methylpyridin-2(1H)-one (from step 2) (3.5 g, 13.2 mmol) was taken up in DMF (10 ml) and cooled to 0° C. 2,4-Difluorobenzyl bromide (1.7 ml, 13.2 mmol) and K2CO3 (1.8 g, 13.2 mmol) were added and the reaction stirred for 6 hours. The reaction was worked up by adding saturated NaHCO3 (aq.) and extracting with ethyl acetate. The ethyl acetate extraction was washed with water, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and dried over Na2SO4, filtered, and the solvent removed in vacuo. The product was obtained in 83% crude yield and carried through to the next step as a brown oil. LC/MS, tr=2.48 minutes (5 to 95% acetonitrile/water over 5 minutes at 1 ml/min with detection 254 nm, at 50° C.). ES-MS m/z 392 (M+H). ES-HRMS m/z 392.0853 (M+H calcd for C20H17ClF2NO3 requires 392.0860).

후처리

  1. extractionextracting with ethyl acetate
  2. extractionThe ethyl acetate extraction
  3. washwas washed with water
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe product was obtained in 83% crude yield

출처 및 근거

ORD 기록
ord-ace715993540483a9518d4c4b75ba249
출처 데이터셋
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07629363B2

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