Sodium Carbonate → HCID 18507798, compound

HRID 1355674Notes

Reaction equation

HRID 1355674 reaction equation
Br[C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([C:6]([CH2:31][C:32]3[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=3)([CH2:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)[C:7](=[O:23])[N:8]2[CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:44]([C:46]1[CH:51]=[CH:50][C:49](B(O)O)=[CH:48][CH:47]=1)#[N:45]>C1(C)C=CC=CC=1.CCO.O.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>[CH3:11][C:10]1[C:2]([C:49]2[CH:50]=[CH:51][C:46]([C:44]#[N:45])=[CH:47][CH:48]=2)=[CH:3][CH:4]=[C:5]2[C:9]=1[N:8]([CH2:12][C:13]1[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=1)[C:7](=[O:23])[C:6]2([CH2:31][C:32]1[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=1)[CH2:24][C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 18507782HCID 18507782, compound

Product 1

HCID 18507798HCID 18507798, compoundYield 93.1%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-bromo-7-methyl-1-naphthalen-2-ylmethyl-3,3-bis-pyridin-4-ylmethyl-1,3-dihydro-indol-2-one (200 mg, 0.365 mmol) in 4 ml of toluene and 2.5 ml of EtOH was added tetrakis(triphenylphosphine)palladium (17 mg, 0.015 mmol) under an atmosphere of dry N2, followed by the addition of a solution of aqueous sodium carbonate (Na2CO3) (77 mg, 0.738 mmol) dissolved in 2 ml of water and 4-cyanobenzene boronic acid (101 mg, 0.686 mmol). The reaction mixture was heated to 100° C. and stirred at this temperature overnight. The reaction mixture was concentrated under vacuum and then partitioned between DCM and saturated aqueous NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated under vacuum to give the crude product. It was chromatographed on silica gel eluting MeOH/NH4OH/CHCl3/(3/0.3/97) to give the titled compound of Example 10 (194 mg, 93% yield).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompartitioned between DCM and saturated aqueous NaHCO3
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give the crude product
  7. customIt was chromatographed on silica gel
  8. washeluting MeOH/NH4OH/CHCl3/(3/0.3/97)

Sources & evidence

ORD record
ord-b4c5655030ad4f59a94d8a10ae9149e6
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

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