Hydrochloric Acid → (spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one-5-yl)boronic acid

HRID 7012

반응식

HRID 7012 반응식
Br[CH:2]1[C:6]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]2=[O:15])[CH2:5][CH2:4][CH2:3]1.[H-].[Na+].C([Li])CCC.C([O:26][B:27](OC(C)C)[O:28]C(C)C)(C)C.Cl>C1COCC1>[NH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2([CH:2]([B:27]([OH:28])[OH:26])[CH2:3][CH2:4][CH2:5]2)[C:7]1=[O:15]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 24758Sodium hydrideHCID 219862275-Bromo-spiro [cyclopentane-1,3'-[3h]indol]-2'(1'h)-oneHCID 178418339Butyllithium

생성물 1

HCID 21986244(spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one-5-yl)boronic acid수율 64%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 5-bromo-spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one (13.1 g, 53 mmol) in anhydrous THF (300 cm3) under N2, was added sodium hydride (60% in mineral oil, 2.1 g, 53 mmol). After 30 minutes, the reaction mixture was cooled to −78° C. and butyl lithium (2.5 M in hexanes, 22 cm3, 53 mmol) was added slowly. After 30 minutes, tris-iso-propylborate (34 cm3, 146 mmol) was added, and the reaction mixture was slowly brought to room temperature, and stirred for 14 hours. The reaction mixture was poured into 1N HCl and extracted with EtOAc (×3). The organic layers were collected and washed with 1N HCl, water, dried (MgSO4) and evaporated to give the subtitled compound (7.8 g, 64%) as a tan solid which was used without further purification. 1H NMR (DMSO-d6) δ 10.3 (s, 1H), 7.9 (s, 1H), 7.7–7.6 (m, 2H), 6.8 (d, 1H, J=7.7 Hz), 3.4 (s, 1H), 2.0–1.7 (m, 8H); MS (FI-POS) m/z @231.

후처리

  1. waitAfter 30 minutes
  2. customwas slowly brought to room temperature
  3. extractionextracted with EtOAc (×3)
  4. customThe organic layers were collected
  5. washwashed with 1N HCl, water
  6. dry with materialdried (MgSO4)
  7. customevaporated

출처 및 근거

ORD 기록
ord-ed84227053dd4cc8ab8a2904657eb785
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084168B2

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