Sodium Carbonate → HCID 178481035, compound

HRID 1013845Notes

Reaction equation

HRID 1013845 reaction equation
Br[C:2]1[CH:23]=[CH:22][C:5]([CH2:6][CH:7]2[CH2:11][CH2:10][N:9]([CH:12]3[CH2:20][CH2:19][C:18]4[C:14](=[CH:15][NH:16][N:17]=4)[CH2:13]3)[C:8]2=[O:21])=[C:4]([Cl:24])[CH:3]=1.Cl.[CH3:26][N:27]1[CH2:32][CH2:31][N:30]([C:33]([C:35]2[CH:40]=[CH:39][C:38](B3OC(C)(C)C(C)(C)O3)=[CH:37][CH:36]=2)=[O:34])[CH2:29][CH2:28]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.O>[Cl:24][C:4]1[CH:3]=[C:2]([C:38]2[CH:37]=[CH:36][C:35]([C:33]([N:30]3[CH2:31][CH2:32][N:27]([CH3:26])[CH2:28][CH2:29]3)=[O:34])=[CH:40][CH:39]=2)[CH:23]=[CH:22][C:5]=1[CH2:6][CH:7]1[CH2:11][CH2:10][N:9]([CH:12]2[CH2:20][CH2:19][C:18]3[C:14](=[CH:15][NH:16][N:17]=3)[CH2:13]2)[C:8]1=[O:21]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 56776829HCID 56776829, compoundHCID 178515501HCID 178515501, compound

Product 1

HCID 178481035HCID 178481035, compoundYield 13%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 3-(4-Bromo-2-chloro-benzyl)-1-(4,5,6,7-tetrahydro-2H-indazol-5-yl)-pyrrolidin-2-one (Example 6) (0.471, 1.16 mmol) in DME (5.0 mL) and de-gas with a stream of nitrogen for 5.0 minutes. Add (4-Methyl-piperazin-1-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone hydrochloride (0.1.14 g, 1.58 mmol), followed by 2.0 M sodium carbonate (2.03 mL, 4.06 mmol) and continue de-gas. Add Pd(Ph3)4 (0.134 g, 0.116 mmol) and heat to 80° C. for 17 hours. Dilute with ethyl acetate and water, separate and save both layers. The pH of the aqueous layer adjusted to ph 9 with 1.0 N HCl, and back extract with three portions of ethyl acetate. The organic layers are combined, dry over sodium sulfate and evaporate. Chromatography (silica 95:5 CH2Cl2/MeOH/1% NH3) yields 0.08 g (0.6%) of the title compound as an amorphorous foam. MS (m/z): 533 (M+1).

Workup

  1. customde-gas with a stream of nitrogen for 5.0 minutes
  2. customcontinue de-gas
  3. customseparate
  4. extractionback extract with three portions of ethyl acetate
  5. dry with materialdry over sodium sulfate
  6. customevaporate

Sources & evidence

ORD record
ord-e14e21da90af467f93d108b71306e27e
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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