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

HRID 1986224노트

반응식

HRID 1986224 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4d607a1d1d4c4454a277760f91a77777
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547691B2

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