Borate → (6-Ethoxy-5-(trifluoromethyl)pyridin-3-yl)boronic acid

HRID 1455198ノート

反応式

HRID 1455198 の反応式
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]([C:16]([F:19])([F:18])[F:17])[C:10]([O:13][CH2:14][CH3:15])=[N:11][CH:12]=1.[B:20]([O-])([O-:22])[O-:21]>CCOCC>[CH2:14]([O:13][C:10]1[C:9]([C:16]([F:19])([F:18])[F:17])=[CH:8][C:7]([B:20]([OH:22])[OH:21])=[CH:12][N:11]=1)[CH3:15]

参加物

5

反応物 3

HCID 26574BorateHCID 673899755-Bromo-2-ethoxy-3-(trifluoromethyl)pyridineHCID 178418339Butyllithium

生成物 1

HCID 67389387(6-Ethoxy-5-(trifluoromethyl)pyridin-3-yl)boronic acid収率 78.6%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Alternatively, n-butyl lithium (1.6 M solution in hexane, 0.9 mL, 1.43 mmol) was slowly added to a solution of 5-bromo-2-ethoxy-3-trifluoromethyl-pyridine (352 mg, 1.3 mmol) in 2.6 mL anhydrous Et2O at −78° C. under nitrogen. The mixture was kept at −78° C. for 1 hr, and then to this mixture was added triisoporpyl borate (489 mg, 2.6 mmol). The mixture was allowed to warm to ambient temperature overnight. The reaction was quenched by water and the pH was adjusted to 5 by carefully addition of 1N aqueous HCl. Two layers were separated and the aqueous layer was extracted with ethyl acatate three times. The extract was washed with brine, dried over sodium sulfate, and concentrated in vacuo to give 2-ethoxy-3-trifluoromethylpyridine-5-boronic acid as a brown oil (240 mg, 67% yield). The product was used for the next step without purification.

後処理

  1. customThe reaction was quenched by water
  2. additionthe pH was adjusted to 5 by carefully addition of 1N aqueous HCl
  3. customTwo layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acatate three times
  5. washThe extract was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7c39fe0fee874e0f8b4785453007688d
出典データセット
uspto-grants-2009_01
特許番号
US07482366B2

反応ノート

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