Sodium Carbonate → HCID 22273801, compound

HRID 1064379Notes

Reaction equation

HRID 1064379 reaction equation
Br[C:2]1[C:7]2[CH2:8][CH2:9][CH:10]([C:14]([N:16]3[CH2:21][CH2:20][CH:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:18][CH2:17]3)=[O:15])[CH2:11][C:12](=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:34]1(B(O)O)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[NH4+].[OH-]>C1(C)C=CC=CC=1.CO.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.O.C(Cl)Cl>[C:34]1([C:2]2[C:7]3[CH2:8][CH2:9][CH:10]([C:14]([N:16]4[CH2:21][CH2:20][CH:19]([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH2:18][CH2:17]4)=[O:15])[CH2:11][C:12](=[O:13])[C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

10

Reactant 4

HCID 10340Sodium Carbonate2×HCID 14923Ammonium HydroxideHCID 66827Phenylboronic AcidHCID 22273732HCID 22273732, compound

Product 1

HCID 22273801HCID 22273801, compoundYield 101.2%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

0.6 g (1.54 mmol) of (±)-1-bromo-7-[(4-phenylpiperidin-1-yl)carbonyl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one were dissolved in 5 mL of toluene under a nitrogen atmosphere, then 54 mg (0.016 mmol) of Pd(PPh3)4 were added, followed by 1.5 mL of 2M Na2CO3 solution and 225 mg (1.85 mmol) of benzeneboronic acid dissolved in 2 mL of MeOH. The resulting heterogeneous mixture was refluxed for 8 h under vigorous stirring, then after cooling it was taken up with CH2Cl2 and water. 8 mL of 2M Na2CO3 solution and 1 mL of conc. NH4OH were added, the organic layer was collected and dried, the solvent was removed in vacuo, yielding 660 mg of the title product which was used without further purification.

Workup

  1. temperatureThe resulting heterogeneous mixture was refluxed for 8 h under vigorous stirring
  2. temperatureafter cooling it
  3. customthe organic layer was collected
  4. customdried
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9418ca49d69d43198c1fe33973bf732d
Source dataset
uspto-grants-2005_11
Patent number
US06969724B2

Reaction notes

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