Sodium Carbonate → HCID 18507795, compound

HRID 1355664Notes

Reaction equation

HRID 1355664 reaction equation
[C:1]12([CH2:11][N:12]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18](Br)[CH:19]=4)[CH2:14][C:13]3=[O:22])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([O-])([O-])=O.[Na+].[Na+].[C:29]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)#[N:30]>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>[C:1]12([CH2:11][N:12]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([C:34]5[CH:35]=[CH:36][C:31]([C:29]#[N:30])=[CH:32][CH:33]=5)[CH:19]=4)[CH2:14][C:13]3=[O:22])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 18507787HCID 18507787, compound

Product 1

HCID 18507795HCID 18507795, compoundYield 36.1%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
100 °C

Procedure

1-Adamantan-1-ylmethyl-6-bromo-1,3-dihydro-indol-2-one (1.06 g, 2.9 mmol) was dissolved in a previously degassed solution of 18 ml of toluene and 3 ml of EtOH under an atmosphere of dry N2. To this solution was added tetrakis(triphenylphosphine)palladium (0) (133 mg, 0.12 mmol) followed by a solution of Na2CO3 (707 mg, 6.67 mmol) dissolved in 5 ml of water. To this solution was added 4-cyanobenzene boronic acid (640 mg, 4.35 mmol) and the reaction mixture was then heated to 100° C. and reacted at this temperature for 4 hours. The reaction mixture was then cooled to ambient temperature and partitioned between DCM and saturated aqueous NaHCO3. The aqueous layer was extracted two more times with DCM and the DCM extracts were then combined and washed with brine. The organic layer was then dried over Na2SO4, filtered and concentrated under vacuum to give a brown oil which was then triturated with Et2O to give 400 mg of the titled compound as a tan oil.

Workup

  1. customreacted at this temperature for 4 hours
  2. temperatureThe reaction mixture was then cooled to ambient temperature
  3. custompartitioned between DCM and saturated aqueous NaHCO3
  4. extractionThe aqueous layer was extracted two more times with DCM
  5. washwashed with brine
  6. dry with materialThe organic layer was then dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto give a brown oil which
  10. customwas then triturated with Et2O

Sources & evidence

ORD record
ord-0e684bd32e254a2ba2d8027a8487d518
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

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