Citric Acid → 2-(Difluoromethyl)-3-fluoropyridine-4-carboxylic acid

HRID 1426287노트

반응식

HRID 1426287 반응식
[F:1][CH:2]([F:14])[C:3]1[C:4]([F:13])=[C:5]([CH:10]=[CH:11][N:12]=1)[C:6]([O:8]C)=[O:7].O.[OH-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.O>[F:14][CH:2]([F:1])[C:3]1[C:4]([F:13])=[C:5]([CH:10]=[CH:11][N:12]=1)[C:6]([OH:8])=[O:7]

참가 물질

6

반응물 3

HCID 311Citric AcidHCID 168937Lithium hydroxide, monohydrateHCID 696732014-Pyridinecarboxylic acid, 2-(difluoromethyl)-3-fluoro-, methyl ester

생성물 1

HCID 696736882-(Difluoromethyl)-3-fluoropyridine-4-carboxylic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 2-(difluoromethyl)-3-fluoroisonicotinate (0.44 g, 2.1 mmol, from Step 4) in tetrahydrofuran (10 mL) was added a solution of lithium hydroxide monohydrate (0.45 g, 11 mmol) in water (10 mL). The reaction was stirred for 2 hours. The reaction mixture was acidified by the addition of a solution of citric acid. The product was extracted with three portions of DCM. The combined extracts were dried over sodium sulfate, decanted and concentrated to afford product, which was used without further purification in Step 6. H NMR (300 MHz, CD3OD): δ 8.57 (d, 1H), 7.99 (dd, 1H), 6.96 (t, 1H).

후처리

  1. extractionThe product was extracted with three portions of DCM
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. customdecanted
  4. concentrationconcentrated
  5. customto afford product, which
  6. customwas used without further purification in Step 6

출처 및 근거

ORD 기록
ord-7a501e3dcb0c45dc98022dcd473e5a34
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933085B2

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