Potassium Carbonate → HCID 58387200, compound

HRID 1045114Notes

Reaction equation

HRID 1045114 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O:11][C:12](=[O:26])[CH2:13][CH2:14][C:15]1[NH:19][C:18]2[CH:20]=[C:21]([Cl:25])[C:22](Br)=[CH:23][C:17]=2[N:16]=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:25][C:21]1[C:22]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:23][C:17]2[N:16]=[C:15]([CH2:14][CH2:13][C:12]([OH:11])=[O:26])[NH:19][C:18]=2[CH:20]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 58387105HCID 58387105, compound2×

Product 1

HCID 58387200HCID 58387200, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

A 4 mL vial with a septum cap and a stirring bar was charged with phenylboronic acid (4.5 mg, 0.037 mmol) and Pd(PPh3)4 (2.0 mg, 5 mol %) and was purged briefly with N2. A solution of 3-(5-bromo-6-chloro-1H-benzimidazol-2-yl)-propionic acid methyl ester (Intermediate 9, 10.0 mg, 0.032 mmol) in DME (200 uL) was added to the vial, followed 1M aqueous K2CO3 (100 uL). The resulting mixture was stirred at 85° C. for 10 h. The mixture was allowed to cool down to rt, and was partitioned with EtOAc (1 mL) and 10% aqueous AcOH (1 mL). The organic layer was separated and evaporated to dryness in vacuo. The resulting oily residue was dissolved in DMSO (1.0 mL), filtered and purified by reverse-phase HPLC to give the title compound. LR-MS (API-ES): calculated for C16H13ClN2O2 300.0, observed m/e 301.0 (M+H)+ (Rt 2.42 min).

Workup

  1. customA 4 mL vial with a septum cap
  2. customwas purged briefly with N2
  3. temperatureto cool down to rt
  4. customwas partitioned with EtOAc (1 mL) and 10% aqueous AcOH (1 mL)
  5. customThe organic layer was separated
  6. customevaporated to dryness in vacuo
  7. dissolutionThe resulting oily residue was dissolved in DMSO (1.0 mL)
  8. filtrationfiltered
  9. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-2f41293bb3c34ddf9d8b001bd82d0c9b
Source dataset
uspto-grants-2013_10
Patent number
US08563746B2

Reaction notes

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