Triethylborane → HCID 9970412, compound

HRID 1824804Notes

Reaction equation

HRID 1824804 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=3Br)[S:9][C:5]=2[CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(B(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C=O)C.ClCCl.[Pd](Cl)Cl.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]>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[N:7]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=3)[S:9][C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 7357TriethylboraneHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 22144554HCID 22144554, compound

Product 1

HCID 9970412HCID 9970412, compoundYield 38.3%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 6-methoxy-2-(2-bromo-3-methoxy-phenyl)-benzothiazole (0.182, 0.52 mmol) in dry DMF (3 mL) was added cesium carbonate (0.51 g, 1.57 mmol), triethylborane (0.58 mL, 1M in THF, 0.58 mmol) and 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride dichloromethane (18 mg, 0.022 mmol). The mixture was heated to 50° C. for 24 h, then cooled to room temperature. Saturated sodium bicarbonate was added and the mixture was extracted with ethylacetate. Combined ethylacetate were washed with brine, concentrated. After chromatographic purification gave 6-methoxy-2-(3-methoxy-phenyl)-benzothiazole (54 mg, 38% yield) as a white solid. Mass spec: MH+=272.

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethylacetate
  3. washCombined ethylacetate were washed with brine
  4. concentrationconcentrated
  5. customAfter chromatographic purification

Sources & evidence

ORD record
ord-028ee8b0118f4ab2b5262db55e64423a
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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