2-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 1-{2-Biphenyl-4-yl-1-phenyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-ethyl)-1H-benzotriazole

HRID 724634

反応式

HRID 724634 の反応式
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH:8]([N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]=[N:16]2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.C([Li])CCC.Br[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([B:43]2[O:47][C:46]([CH3:49])([CH3:48])[C:45]([CH3:51])([CH3:50])[O:44]2)=[CH:39][CH:38]=1>O1CCCC1>[C:1]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:2]=[CH:3][C:4]([CH2:7][C:8]([N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]=[N:16]2)([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:36][C:37]2[CH:38]=[CH:39][C:40]([B:43]3[O:44][C:45]([CH3:51])([CH3:50])[C:46]([CH3:49])([CH3:48])[O:47]3)=[CH:41][CH:42]=2)=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 218795131-(2-Biphenyl-4-yl-1-phenyl-ethyl)-1H-benzotriazoleHCID 178418339Butyllithium

生成物 1

HCID 218794011-{2-Biphenyl-4-yl-1-phenyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-ethyl)-1H-benzotriazole収率 50%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

A solution of 4.26-A of Step 1 (450 mg, 1.2 mmol) in tetrahydrofuran (14 mL) was cooled to −78° C. and treated with n-butyllithium (0.62 mL, 2.5 M in hexanes) dropwise. The reaction mixture was stirred at −78° C. for 10 min and 2-[4-(bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (410 mg, 1.4 mmol) in tetrahydrofuran (2 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 1 h, quenched with sat. ammonium chloride (2 mL), and extracted with ethyl acetate (15 mL). The organic layer was separated and washed with brine (5 mL), dried with sodium sulfate, filtered, and concentrated to a crude residue which was purified by flash column chromatography to yield the desired product (350 mg, 50%). LCMS found for C39H38BN3O2Na (M+Na)+: m/z=614.

後処理

  1. stirringThe reaction mixture was stirred at −78° C. for 1 h
  2. customquenched with sat. ammonium chloride (2 mL)
  3. extractionextracted with ethyl acetate (15 mL)
  4. customThe organic layer was separated
  5. washwashed with brine (5 mL)
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to a crude residue which
  9. customwas purified by flash column chromatography

出典と根拠

ORDレコード
ord-27c81669459043538a4e152ea99e2258
出典データセット
uspto-grants-2006_11
特許番号
US07141596B2

関連ノート

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