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1,2-Dimethoxyethane → HCID 178515614, compound

HRID 33554
Notes
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Reaction equation

HRID 33554 reaction equation
Br[C:2]1[CH:22]=[CH:21][C:5]2[NH:6][C:7]([NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[C:14]4[C:19]=3[CH:18]=[C:17]([OH:20])[CH:16]=[CH:15]4)=[N:8][C:4]=2[CH:3]=1.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])([O-])=O.[Na+].[Na+].O.C(COC)OC>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCO>[C:23]1([C:2]2[CH:22]=[CH:21][C:5]3[NH:6][C:7]([NH:9][C:10]4[CH:11]=[CH:12][CH:13]=[C:14]5[C:19]=4[CH:18]=[C:17]([OH:20])[CH:16]=[CH:15]5)=[N:8][C:4]=3[CH:3]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 66827Phenylboronic AcidHCID 2735133Sodium Carbonate MonohydrateHCID 178515612HCID 178515612, compound

Product 1

HCID 178515614HCID 178515614, compound

Reagents, catalysts & solvents 3

HCID 178418476
HCID 178418476, compound
Catalyst
HCID 702EthanolSolvent
HCID 962WaterSolvent2×

Procedure

A mixture of 8-(5-bromo-1H-benzo[d]imidazol-2-ylamino)naphthalen-2-ol (18 mg, 0.05 mmol, Example 14), phenylboronic acid (12 mg, 0.1 mmol, Aldrich), PdCl2(PPh3)2 (3.5 mg, 0.005 mmol, Aldrich), Na2CO3.H2O (12 mg, 0.1 mmol), dimethoxyethane (0.35 mL), H2O (0.15 mL) and EtOH (0.1 1 mL) was subjected to microwave irradiation at 120° C. with stirring for 10 min. The reaction mixture was cooled to room temperature, diluted with water (5 mL) and extracted with EtOAc (2×10 mL). The combined organic phases were washed with brine (10 mL), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile) to give the title compound. MS (ESI, pos. ion) m/z: 352 (M+1).

Workup

  1. customirradiation at 120° C.
  2. extractionextracted with EtOAc (2×10 mL)
  3. washThe combined organic phases were washed with brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile)

Sources & evidence

ORD record
ord-3540a1b0460743118b842ff193bedd8a
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07429608B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes