Sodium Carbonate → HCID 22632689, compound

HRID 2417503Notes

Reaction equation

HRID 2417503 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([N:8]2[CH2:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[NH:11][C:10](=[O:19])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].I[C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1.[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1(C)C=CC=CC=1.O>[C:25]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:32]=[CH:31][C:28]([CH2:29][N:11]2[C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[CH2:14][N:8]([C:6](=[O:7])[C:5]3[CH:20]=[CH:21][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH2:9][C:10]2=[O:19])=[CH:27][CH:26]=1

Participants

11

Reactant 5

HCID 10340Sodium CarbonateHCID 24758Sodium hydrideHCID 66827Phenylboronic AcidHCID 9542584-Iodobenzyl bromideHCID 226325544-(4-Chlorobenzoyl)-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on

Product 1

HCID 22632689HCID 22632689, compound

Reagents, catalysts & solvents 5

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

300 mg (1.0 mmol) of 4-(4-chlorobenzoyl)-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on was dissolved in 10 ml of DMF. 50 mg (1.25 mmol) of sodium hydride was added to the obtained solution, and they were stirred at room temperature for 30 minutes. 300 mg (1.0 mmol) of 4-iodobenzyl bromide was added to the obtained mixture, and they were stirred at room temperature overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the solvent was evaporated, and the obtained crude product was washed with hexane. 30 mg (0.058 mmol) of the obtained product was mixed with 7 mg (0.058 mmol) of phenyl boronic acid, 5 mg of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium, 3 mg of 1,1′-bisdiphenylphosphinoferrocene, 265 mg (2.5 mmol) of sodium carbonate, 1 ml of water and 3 ml of toluene, and the obtained mixture was stirred at 80° C. overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the solvent was evaporated, and the obtained crude product was treated in the same manner as in Step 3 in Example 1 to obtain the title compound.

Workup

  1. stirringwere stirred at room temperature overnight
  2. customAfter the treatment with ethyl acetate as the extracting solvent by an ordinary method, the solvent was evaporated
  3. customthe obtained crude product
  4. washwas washed with hexane
  5. stirringthe obtained mixture was stirred at 80° C. overnight
  6. customAfter the treatment with ethyl acetate as the extracting solvent by an ordinary method, the solvent was evaporated
  7. customthe obtained crude product
  8. additionwas treated in the same manner as in Step 3 in Example 1

Sources & evidence

ORD record
ord-d669c5e7e18844b3a5e09c88f82b0af6
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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