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

반응식

HRID 724634 반응식
[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

참가 물질

5

반응물 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

생성물 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-benzotriazole수율 50%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-27c81669459043538a4e152ea99e2258
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141596B2

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