Sodium Carbonate → Methyl 1-((5-(quinolin-2-ylmethoxy)-1-(3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)benzyl)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylate

HRID 2178475Notes

Reaction equation

HRID 2178475 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][CH:39]=1)[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:27][C:28]1([C:33]([O:35][CH3:36])=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1.[CH3:40][Si:41]([CH3:55])([CH3:54])[CH2:42][CH2:43][O:44][CH2:45][N:46]1[C:50](B(O)O)=[CH:49][CH:48]=[N:47]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[CH:26][C:17]=1[CH2:16][O:15][C:13]1[CH:12]=[CH:11][C:10]2[N:6]([CH2:5][C:4]3[CH:37]=[CH:38][CH:39]=[C:2]([C:50]4[N:46]([CH2:45][O:44][CH2:43][CH2:42][Si:41]([CH3:55])([CH3:54])[CH3:40])[N:47]=[CH:48][CH:49]=4)[CH:3]=3)[C:7]([CH2:27][C:28]3([C:33]([O:35][CH3:36])=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]3)=[N:8][C:9]=2[CH:14]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 21874652(1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)boronic acidHCID 90414509Methyl 1-{[1-(3-bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]methyl}cyclopentane-carboxylate

Product 1

HCID 90414691Methyl 1-((5-(quinolin-2-ylmethoxy)-1-(3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)benzyl)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 5 mL microwave vial were added methyl 1-{[1-(3-bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]methyl}cyclopentane carboxylate (59 mg, 0.1 mmol), Pd(Ph3)4 (10 mg, 0.008 mmol), (1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)boronic acid (65 mg, 0.26 mmol), Na2CO3 (0.15 mL, 2 M) and 1,4-dioxane (1.5 mL). The vial was flushed with N2 then capped and placed in a heating block at 100° C. After 16 h the mixture was cooled to RT, transferred to a round-bottomed flask and concentrated to dryness. The residue was purified using FCC to provide the title compound. MS (ESI): mass calcd. for C41H47N5O4Si, 701.94; m/z found 702.0 [M+H]+.

Workup

  1. customThe vial was flushed with N2
  2. customthen capped
  3. customplaced in a heating block at 100° C
  4. customtransferred to a round-bottomed flask
  5. concentrationconcentrated to dryness
  6. customThe residue was purified

Sources & evidence

ORD record
ord-495b54747c1a4eb88f72cc3573507622
Source dataset
uspto-grants-2015_06
Patent number
US09067917B2

Reaction notes

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