Dichloromethane → HCID 136348999, compound

HRID 2377849Notes

Reaction equation

HRID 2377849 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([NH:9][C:10]1[C:19]3[C:14](=[CH:15][CH:16]=[C:17](Br)[CH:18]=3)[NH:13][C:12](=[O:21])[C:11]=1[C:22]1[NH:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[N:23]=1)[CH2:2]2.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>COCCOC>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@H:3]([NH:9][C:10]1[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:36]4[CH:37]=[CH:38][C:33]([O:32][CH3:31])=[CH:34][CH:35]=4)[CH:18]=3)[NH:13][C:12](=[O:21])[C:11]=1[C:22]1[NH:26][C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[N:23]=1)[CH2:2]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 135430758HCID 135430758, compound

Product 1

HCID 136348999HCID 136348999, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A vial was charged with the hydrochloride salt of 4-[(3S)-1-azabicyclo[2.2.2]oct-3-ylamino]-3-(1H-benzimidazol-2-yl)-6-bromoquinolin-2(1H)-one (1.0 equivalent) and 4-methoxyphenyl boronic acid (1.3 equivalents). To this solution was added DME and 2 M aqueous Na2CO3 (10%). The mixture was degassed by bubbling argon through the solution for 5 minutes. Pd(dppf)2Cl2.CH2Cl2 (0.2 equivalents) was then added to the degassed solution. The mixture was heated at 90° C. for 16 hours, and the top organic layer was separated and filtered. The solvent was removed, and the residue was purified by reverse phase HPLC affording the desired product. MS m/z 492.6 (M+H).

Workup

  1. customThe mixture was degassed
  2. customby bubbling argon through the solution for 5 minutes
  3. customthe top organic layer was separated
  4. filtrationfiltered
  5. customThe solvent was removed
  6. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-789d60d6b3564581aed42b54c390b4e6
Source dataset
uspto-grants-2008_12
Patent number
US07470709B2

Reaction notes

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