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

HRID 1426287ノート

反応式

HRID 1426287 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7a501e3dcb0c45dc98022dcd473e5a34
出典データセット
uspto-grants-2015_01
特許番号
US08933085B2

反応ノート

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