Cesium carbonate → HCID 178515169, compound

HRID 1400113Notes

Reaction equation

HRID 1400113 reaction equation
Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]3[C:13](=[O:14])[N:12]([CH2:15][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:11](=[O:23])[C:9]3=2)[N:4](CC2C=CC(OC)=CC=2)[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:39]1(B(O)O)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN(C)C=O.C(OCC)(=O)C.[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[CH2:15]([N:12]1[C:13](=[O:14])[C:8]2[C:9](=[C:10]3[C:2]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[N:3][NH:4][C:5]3=[N:6][CH:7]=2)[C:11]1=[O:23])[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 595071011-bromo-3-(4-methoxybenzyl)-7-phenethylpyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione

Product 1

HCID 178515169HCID 178515169, compound

Reagents, catalysts & solvents 3

HCID 178454861HCID 178454861, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 1-bromo-3-(4-methoxybenzyl)-7-phenethylpyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione (25 mg, 50 umol), cesium carbonate (32 mg, 100 umol), phenyl boronic acid (12 mg, 100 umol) and 1,1′-bis(di-t-butylphosphino)ferrocene palladium dichloride (2 mg) in anhydrous N,N-dimethylformamide (2 ml) was heated to 180° C. under microwave conditions for 5 minutes. The mixture was diluted with ethyl acetate (50 ml) and washed with dilute brine (4×30 ml), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure then treated with trifluoroacetic acid (1 ml) and heated to 70° C. for 7 hours. The mixture was concentrated under reduced pressure and purified by reverse phase column chromatography to yield 7-phenethyl-1-phenylpyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8(3H,7H)-dione. LCMS: [M+H] 369.

Workup

  1. washwashed with dilute brine (4×30 ml)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionthen treated with trifluoroacetic acid (1 ml)
  6. temperatureheated to 70° C. for 7 hours
  7. concentrationThe mixture was concentrated under reduced pressure
  8. custompurified by reverse phase column chromatography

Sources & evidence

ORD record
ord-7a0189a00ee24871a52de06bb6dbffac
Source dataset
uspto-grants-2014_12
Patent number
US08906928B2

Reaction notes

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