Potassium Carbonate → HCID 68659508, compound

HRID 1945292Notes

Reaction equation

HRID 1945292 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:34]([Cl:35])=[CH:33][C:17]3[NH:18][C:19]([O:21][C:22]4[CH:23]=[CH:24][C:25]([CH3:32])=[C:26]([CH:31]=4)[C:27]([O:29][CH3:30])=[O:28])=[N:20][C:16]=3[CH:15]=2)=[CH:10][CH:9]=1.[F:36][C:37]1[CH:38]=[C:39](B(O)O)[CH:40]=[CH:41][CH:42]=1>O1CCOCC1.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:35][C:34]1[C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:41]3[CH:40]=[CH:39][CH:38]=[C:37]([F:36])[CH:42]=3)=[CH:9][CH:10]=2)=[CH:15][C:16]2[N:20]=[C:19]([O:21][C:22]3[CH:23]=[CH:24][C:25]([CH3:32])=[C:26]([CH:31]=3)[C:27]([O:29][CH3:30])=[O:28])[NH:18][C:17]=2[CH:33]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 68532153HCID 68532153, compound

Product 1

HCID 68659508HCID 68659508, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

K2CO3 (1 M in water) (0.16 mL, 0.162 mmol) was added to a solution of methyl 5-{[5-(4-bromophenyl)-6-chloro-1H-benzimidazol-2-yl]oxy}-2-methylbenzoate (25.5 mg, 0.054 mmol), 3-fluorophenylboronic acid (9 mg, 0.068 mmol) and Pd(PPh3)4 (6 mg) in dioxane (1 mL). The reaction was microwaved at 150° C. for 8 minutes. Volatiles were removed. The residue was partitioned between EtOAc (50 mL), and water (50 mL). The aqueous phase was extracted with EtOAc (3×40 mL). Combined organics were washed with brine, dried (MgSO4), filtered and concentrated. Purification by HPLC eluting with 10-90% MeCN:water afforded the desired product.

Workup

  1. customThe reaction was microwaved at 150° C. for 8 minutes
  2. customVolatiles were removed
  3. customThe residue was partitioned between EtOAc (50 mL), and water (50 mL)
  4. extractionThe aqueous phase was extracted with EtOAc (3×40 mL)
  5. washCombined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by HPLC
  10. washeluting with 10-90% MeCN

Sources & evidence

ORD record
ord-a4c301b1aea34bf29416e17eff3198a0
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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