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

Reaction equation

HRID 724634 reaction equation
[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

Participants

5

Reactant 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

Product 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-benzotriazoleYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-27c81669459043538a4e152ea99e2258
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Linked notes

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