Potassium Carbonate → HCID 71073942, compound

HRID 340782Notes

Reaction equation

HRID 340782 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:34]([Cl:35])=[CH:33][C:11]3[N:12]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:13]([O:15][CH:16]4[CH2:19][CH:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:17]4)=[N:14][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[OH:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>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.CN(C=O)C>[Cl:35][C:34]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[OH:36])=[CH:7][CH:6]=2)=[CH:9][C:10]2[N:14]=[C:13]([O:15][CH:16]3[CH2:19][CH:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:17]3)[N:12]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:31])([CH3:32])[CH3:30])[C:11]=2[CH:33]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2773454(2-Hydroxyphenyl)boronic acidHCID 71073922HCID 71073922, compound

Product 1

HCID 71073942HCID 71073942, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A 50 mL flask was charged with ethyl 3-{[5-(4-bromophenyl)-6-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-benzimidazol-2-yl]oxy}cyclobutanecarboxylate (150 mg, 0.259 mmol), 2-hydroxybenzeneboronic acid, pinacol ester (60 mg, 0.273 mmol), Pd(PPh3)4 (20 mg, 0.017 mmol), DMF (5 mL), and 1 M aqueous K2CO3 (0.78 ml, 0.780 mmol). The reaction was degassed with N2 and then heated at 120° C. for 1 hour. Then the volatiles were removed in vacuo and the residue partitioned between EtOAc and H2O. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over (MgSO4), filtered, and concentrated. Chromatography of the resulting residue over silica (preparative TLC) eluting with 45% EtOAc/hexanes afforded the desired product. LC-MS: calculated for C32H37ClN2O5Si 592.22, observed m/e: 593.05 (M+H)+ (Rt 2.67/4 min).

Workup

  1. customThe reaction was degassed with N2
  2. customThen the volatiles were removed in vacuo
  3. customthe residue partitioned between EtOAc and H2O
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washChromatography of the resulting residue over silica (preparative TLC) eluting with 45% EtOAc/hexanes

Sources & evidence

ORD record
ord-96bd535de1d04754b3f22206a9e48ad9
Source dataset
uspto-grants-2014_11
Patent number
US08895596B2

Reaction notes

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