Sodium Carbonate → HCID 46205447, compound

HRID 2366462Notes

Reaction equation

HRID 2366462 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1.[C:13]([O:17][C:18]([N:20]1[CH:24]=[CH:23][CH:22]=[C:21]1B(O)O)=[O:19])([CH3:16])([CH3:15])[CH3:14].C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOC.O.C(O)C>[F:12][C:4]1[CH:3]=[C:2]([C:21]2[N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH:24]=[CH:23][CH:22]=2)[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 113453114-Bromo-2-fluoro-benzoic acid methyl ester

Product 1

HCID 46205447HCID 46205447, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Procedure

A mixture of EXAMPLE 50A (4 g), 1-(tert-butoxycarbonyl)pyrrole-2-boronic acid (5.44 g), and dichlorobis(triphenylphosphine)palladium(II) (1.2 g) in 7:3:2 DME/water/ethanol (300 mL) and 2M aqueous Na2CO3 (17.2 mL) at 80° C. was stirred for 140 minutes, cooled and concentrated. The concentrate was dissolved in ethyl acetate, washed with brine and concentrated. The concentrate was flash chromatographed on silica gel with 1:4 ethyl acetate/hexane.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. dissolutionThe concentrate was dissolved in ethyl acetate
  4. washwashed with brine
  5. concentrationconcentrated
  6. customchromatographed on silica gel with 1:4 ethyl acetate/hexane

Sources & evidence

ORD record
ord-d007100f7f8d4a37b9e2f1372625ea99
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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