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

HRID 852508

反応式

HRID 852508 の反応式
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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-15375f9a65f84af99bf0d1af7aba4ffc
出典データセット
uspto-grants-2007_08
特許番号
US07253203B2

関連ノート

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