Triisopropyl borate → 3-cyano-1-cyclobutyl-6-cyclopropyl-1H-indol-2-ylboronic acid

HRID 1027987ノート

反応式

HRID 1027987 の反応式
[CH:1]1([N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([CH:14]4[CH2:16][CH2:15]4)[CH:12]=3)[C:7]([C:17]#[N:18])=[CH:6]2)[CH2:4][CH2:3][CH2:2]1.[B:19](OC(C)C)([O:24]C(C)C)[O:20]C(C)C.[Li+].CC([N-]C(C)C)C>C1COCC1>[C:17]([C:7]1[C:8]2[C:13](=[CH:12][C:11]([CH:14]3[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)[N:5]([CH:1]2[CH2:4][CH2:3][CH2:2]2)[C:6]=1[B:19]([OH:24])[OH:20])#[N:18]

参加物

5

反応物 3

HCID 21531Triisopropyl borateHCID 2724682Lithium diisopropylamideHCID 667308071-cyclobutyl-6-cyclopropyl-1H-indole-3-carbonitrile

生成物 1

HCID 667305423-cyano-1-cyclobutyl-6-cyclopropyl-1H-indol-2-ylboronic acid収率 105.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

Into a solution of 1-cyclobutyl-6-cyclopropyl-1H-indole-3-carbonitrile (2.0 g, 8.47 mmol) and triisopropyl borate (3.52 mL, 15.25 mmol) in THF (35 mL) at −78° C. was added LDA (1.5 M in cyclohexane, 7.3 mL, 11.01 mmol). The mixture was stirred at −78° C. for 30 min, quenched with ice water (60 mL) and stirred for 15 min without cooling. The mixture was extracted with ethyl acetate 1:1 in hexane (20 mL). The aqueous layer was acidified with 2 N aq. HCl to pH 5 and then extracted with CH2Cl2 (60 mL). The organic layer was dried over Na2SO4 and concentrated to give the title compound as a solid (2.5 g, 70% pure by LCMS) that was used in the next step without further purification.

後処理

  1. customquenched with ice water (60 mL)
  2. stirringstirred for 15 min
  3. temperaturewithout cooling
  4. extractionThe mixture was extracted with ethyl acetate 1:1 in hexane (20 mL)
  5. extractionextracted with CH2Cl2 (60 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-1c05e00150f1403f91a48fdc3cbdc2ae
出典データセット
uspto-grants-2014_05
特許番号
US08735414B2

反応ノート

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