Sodium Carbonate → HCID 18507795, compound

HRID 1355671Notes

Reaction equation

HRID 1355671 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.C(O)C.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 30.3%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
100 °C

Procedure

To a solution of 1-adamantan-1-ylmethyl-6-bromo-1,3-dihydro-indol-2-one (1.85 g, 5.13 mmol) in toluene (23 ml) and ethanol (21 ml) were added tetrakis(triphenylphosphine)palladium (0.60 g, 0.513 mmol), sodium carbonate (1.09 g, 10.27 mmol) in water (11 ml) and solid 4-cyanophenylboronic acid (1.51 g, 10.27 mmol). The mixture was heated at 100° C. overnight. The reaction mixture was partitioned between chloroform and aqueous saturated potassium carbonate (50 ml). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under vacuum to give the crude product. This was chromatographed on flash silica gel eluting with a 15% ethyl acetate in hexane to give the title compound of 9C as a white solid (0.594 g, 30.3% yield).

Workup

  1. customThe reaction mixture was partitioned between chloroform and aqueous saturated potassium carbonate (50 ml)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give the crude product
  7. customThis was chromatographed on flash silica gel eluting with a 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9276da574c6e4592aaea0ec205cb4077
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

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