Diisopropylamine → (4-Carboxybenzo[b]thiophen-2-yl)boronic acid

HRID 1986224ノート

反応式

HRID 1986224 の反応式
C([Li])CCC.C(NC(C)C)(C)C.[S:13]1[CH:17]=[CH:16][C:15]2[C:18]([C:22]([OH:24])=[O:23])=[CH:19][CH:20]=[CH:21][C:14]1=2.[B:25](OC(C)C)([O:30]C(C)C)[O:26]C(C)C>C1COCC1>[C:22]([C:18]1[C:15]2[CH:16]=[C:17]([B:25]([OH:30])[OH:26])[S:13][C:14]=2[CH:21]=[CH:20][CH:19]=1)([OH:24])=[O:23]

参加物

6

反応物 4

HCID 7912DiisopropylamineHCID 21531Triisopropyl borateHCID 1051638Benzo[b]thiophene-4-carboxylic acidHCID 178418339Butyllithium

生成物 1

HCID 67272237(4-Carboxybenzo[b]thiophen-2-yl)boronic acid収率 80.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

n-Butyllithium (2.5 M, 94 mL) is added dropwise to a stirred solution of diisopropylamine (33.0 mL, 235 mmol) in anhydrous THF (300 mL) at −78° C. under nitrogen atmosphere. After 30 minutes, a solution of benzo[b]thiophene-4-carboxylic acid (20.0 g, 112 mmol) in anhydrous THF (300 mL) is added. Upon the completion of addition, the reaction mixture is allowed to warm up to 0° C. where it is stirred for another 2 hours. The reaction mixture is cooled to −30° C. before it is treated with triisopropyl borate (65.0 mL, 282 mmol). The cooling bath is then removed and the reaction is allowed to reach ambient temperature where it is carefully quenched with concentrated HCl (200 mL). After evaporation of THF a suspension is formed, the solid is collected by filtration, washed twice with water (150 mL×2) and dried to provide the title compound as a white solid (20.0 g, 80% yield).

後処理

  1. additionUpon the completion of addition
  2. temperatureThe reaction mixture is cooled to −30° C. before it
  3. customThe cooling bath is then removed
  4. customto reach ambient temperature
  5. customis carefully quenched with concentrated HCl (200 mL)
  6. customAfter evaporation of THF a suspension
  7. customis formed
  8. filtrationthe solid is collected by filtration
  9. washwashed twice with water (150 mL×2)
  10. customdried

出典と根拠

ORDレコード
ord-4d607a1d1d4c4454a277760f91a77777
出典データセット
uspto-grants-2009_06
特許番号
US07547691B2

反応ノート

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