1,2-Dimethoxyethane → HCID 10028858, compound

HRID 747128Notes

Reaction equation

HRID 747128 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:11]3[N:12]=[N:13][C:14](Cl)=[C:15]([C:17]4[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=4)[CH:16]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][C:29]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C(COC)OC>C(OCC)(=O)C.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.O.CCO>[S:1]1[C:5]2[CH:6]=[C:7]([NH:10][C:11]3[N:12]=[N:13][C:14]([C:30]4[CH:29]=[CH:28][C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[CH:31]=4)=[C:15]([C:17]4[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=4)[CH:16]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

9

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734375(Naphthalen-2-yl)boronic acidHCID 9978709HCID 9978709, compound

Product 1

HCID 10028858HCID 10028858, compound

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

(Ph3P)2PdCl2 (0.026 g, 0.038 mmol, Strem) was added to a mixture of benzothiazol-6-yl-[6-chloro-5-(4-trifluoromethylphenyl)pyridazin-3-yl]amine (0.203 g, 0.5 mmol, Example 81(e), 2-naphthaleneboronic acid (0.129 g, 0.75 mmol, Aldrich), Na2CO3 (0.053 g, 0.5 mmol), dimethoxyethane (1.4 mL), EtOH (0.4 mL) and water (0.6 mL). The reaction mixture was heated in a microwave at 120° C. for 15 min with stirring under nitrogen. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (50 mL), washed with 1N NaOH (20 mL) and water (2×20 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel chromatography with ethyl acetate/hexane (1:1) to give the title compound as an yellow amorphous solid. MS (ESI, pos. ion) m/z: 499 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with 1N NaOH (20 mL) and water (2×20 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-086c2f50ef384e34b50f60260564db0c
Source dataset
uspto-grants-2008_07
Patent number
US07396831B2

Reaction notes

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