Dichloromethane → Methyl 1-((1-((4'-(methylsulfonamido)-[1,1'-biphenyl]-3-yl)methyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylate

HRID 2178452Notes

Reaction equation

HRID 2178452 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.C(Cl)Cl.CC1(C)C(C)(C)OB([C:51]2[CH:56]=[CH:55][C:54]([NH:57][S:58]([CH3:61])(=[O:60])=[O:59])=[CH:53][CH:52]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1>[CH3:61][S:58]([NH:57][C:54]1[CH:53]=[CH:52][C:51]([C:2]2[CH:39]=[CH:38][CH:37]=[C:4]([CH2:5][N:6]3[C:10]4[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]5[CH:26]=[CH:25][C:24]6[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=6)[N:18]=5)=[CH:14][C:9]=4[N:8]=[C:7]3[CH2:27][C:28]3([C:33]([O:35][CH3:36])=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32]3)[CH:3]=2)=[CH:56][CH:55]=1)(=[O:60])=[O:59]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 16217653N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamideHCID 90414509Methyl 1-{[1-(3-bromobenzyl)-5-(quinolin-2-ylmethoxy)-1H-benzimidazol-2-yl]methyl}cyclopentane-carboxylate

Product 1

HCID 90416392Methyl 1-((1-((4'-(methylsulfonamido)-[1,1'-biphenyl]-3-yl)methyl)-5-(quinolin-2-ylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)cyclopentanecarboxylate

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 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}cyclopentanecarboxylate (126 mg, 0.21 mmol), Pd(dppf)Cl2.DCM (18 mg, 0.02 mmol), N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (192 mg, 0.65 mmol), Na2CO3 (0.3 mL, 2 M) and 1,4-dioxane (2.5 mL). The vial was flushed with N2 then capped and placed in a heating block at 80° C. After 16 h mixture was cooled to RT, transferred to a round-bottomed flask and was concentrated to dryness. The residue was purified using FCC to provide the title compound. MS (ESI): mass calcd. for C39H38N4O5S, 674.82; m/z found, 675.2 [M+H]+.

Workup

  1. customThe vial was flushed with N2
  2. customthen capped
  3. customplaced in a heating block at 80° C
  4. customtransferred to a round-bottomed flask
  5. concentrationwas concentrated to dryness
  6. customThe residue was purified

Sources & evidence

ORD record
ord-51692109fc26454487f5ac2934d3beca
Source dataset
uspto-grants-2015_06
Patent number
US09067917B2

Reaction notes

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