Pyrrolidine → Methyl 1-((1-(3-(pyrrolidin-1-yl)benzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylate

HRID 2178487Notes

Reaction equation

HRID 2178487 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.CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C.[NH:73]1[CH2:77][CH2:76][CH2:75][CH2:74]1>CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C.C1(C)C=CC=CC=1>[N:73]1([C:2]2[CH:3]=[C:4]([CH:37]=[CH:38][CH:39]=2)[CH2:5][N:6]2[C:10]3[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]4[CH:26]=[CH:25][C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[N:18]=4)=[CH:14][C:9]=3[N:8]=[C:7]2[CH2:27][C:28]2([C:33]([O:35][CH3:36])=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:77][CH2:76][CH2:75][CH2:74]1

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylHCID 90414509Methyl 1-{[1-(3-bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]methyl}cyclopentane-carboxylate

Product 1

HCID 90414147Methyl 1-((1-(3-(pyrrolidin-1-yl)benzyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylateYield 45.7%

Reagents, catalysts & solvents 2

HCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylCatalystHCID 1140TolueneSolvent

Procedure

To a 5 mL microwave vial were added methyl 1-{[1-(3-bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]methyl}cyclopentanecarboxylate (50.5 mg, 0.08 mmol), RuPhos (4.1 mgs, 0.008 mmol), RuPhos pre-catalyst (7.1 mg, 0.009 mmol), pyrrolidine (15 μL, 0.17 mmol) and toluene (1.5 mL). The vial was flushed with N2, NaOt-Bu was added (16.2 mg, 0.17 mmol) then capped and placed in a heating block at 100° C. After 6 h the mixture was cooled to RT, transferred to a round-bottomed flask and concentrated to dryness. The resulting residue was purified using FCC to provide 21 mg of the title compound. MS (ESI): mass calcd. for C36H38N4O3, 574.71; m/z found 575.2 [M+H]+.

Workup

  1. customThe vial was flushed with N2, NaOt-Bu
  2. additionwas added (16.2 mg, 0.17 mmol)
  3. customthen capped
  4. customplaced in a heating block at 100° C
  5. customtransferred to a round-bottomed flask
  6. concentrationconcentrated to dryness
  7. customThe resulting residue was purified

Sources & evidence

ORD record
ord-ae4e8f2665da45c2aa2d4bb8b60f22db
Source dataset
uspto-grants-2015_06
Patent number
US09067917B2

Reaction notes

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