Water → [4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl](1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)methanone

HRID 573274Notes

Reaction equation

HRID 573274 reaction equation
[CH3:1][Si:2]([CH3:17])([CH3:16])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[CH:8]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.CON(C)[C:31](=[O:47])[C:32]1[CH:37]=[CH:36][C:35]([B:38]2[O:42][C:41]([CH3:44])([CH3:43])[C:40]([CH3:46])([CH3:45])[O:39]2)=[CH:34][CH:33]=1.O>C1COCC1>[CH3:43][C:41]1([CH3:44])[C:40]([CH3:45])([CH3:46])[O:39][B:38]([C:35]2[CH:34]=[CH:33][C:32]([C:31]([C:8]3[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:17])([CH3:16])[CH3:1])[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[N:9]=3)=[O:47])=[CH:37][CH:36]=2)[O:42]1

Participants

6

Reactant 4

HCID 962WaterHCID 2733832Lithium HexamethyldisilazideHCID 109229071-((2-(Trimethylsilyl)ethoxy)methyl)-1H-benzo[D]imidazoleHCID 46739065N-methoxy-N-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Product 1

HCID 86688959[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl](1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl)methanoneYield 53.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzo[d]imidazole (6.06 g) in THF (50 mL) was added LiHMDS (1 M solution in THF, 30 ml) dropwise at 0° C. After stirring for 1 h, a solution of N-methoxy-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (7.10 g) in THF (50 mL) was added dropwise, and the mixture was stirred for 1 h at 0° C. The reaction mixture was poured into water and extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/AcOEt) and crystallized from hexane to give the title compound (6.20 g). 1H NMR (300 MHz, CDCl3) δ −0.11 (9H, s), 0.84-0.91 (2H, m), 1.37 (12H, s), 3.55-3.62 (2H, m), 6.03 (2H, s), 7.37-7.43 (1H, m), 7.45-7.50 (1H, m), 7.65-7.70 (1H, m), 7.91-7.98 (3H, m), 8.22-8.26 (2H, m).

Workup

  1. stirringthe mixture was stirred for 1 h at 0° C
  2. extractionextracted with AcOEt
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/AcOEt)
  7. customcrystallized from hexane

Sources & evidence

ORD record
ord-28bfb01709c94763a4961172e640c3da
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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