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Sodium Carbonate → HCID 22503541, compound

HRID 1006975
Notes
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Reaction equation

HRID 1006975 reaction equation
[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][C:10](OB(O)O)=[CH:9][CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1.Br[C:18]1[N:19]=[C:20]([N:28]2[CH2:33][CH2:32][N:31]([CH2:34][CH3:35])[CH2:30][CH2:29]2)[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[CH2:34]([N:31]1[CH2:30][CH2:29][N:28]([C:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:27]=[C:18]([C:10]3[CH:11]=[CH:12][C:7]([C:2]4([CH3:1])[O:6][CH2:5][CH2:4][O:3]4)=[CH:8][CH:9]=3)[N:19]=2)[CH2:33][CH2:32]1)[CH3:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 225024471-(1-Ethylpiperazin-4-yl)-3-bromoisoquinolineHCID 22503476HCID 22503476, compound

Product 1

HCID 22503541HCID 22503541, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 1140
Toluene
Solvent

Procedure

4-(2-Methyl-1,3-dioxolan-2-yl)phenylboric acid (0.41 g) and 3-bromo-1-(4-ethylpiperazin-1-yl)isoquinoline (0.62 g) were reacted in the presence of tetrakistriphenylphosphinepalladium(0) (0.11 g) in toluene (50 ml) and a 10% aqueous solution of sodium carbonate (30 ml) in nitrogen atmosphere at 120° C. for 30 min. The organic layer was separated, washed with brine and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol system), to give 1-(4-ethylpiperazin-1-yl)-3-[4-(2-methyl-1,3-dioxolan-2-yl)phenyl]isoquinoline.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol system)

Sources & evidence

ORD record
ord-a687b47510ce4938ab507a4e3a60f42b
Source dataset
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06790844B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes