HCID 70558051, compound → HCID 70558071, compound

HRID 1503810Notes

Reaction equation

HRID 1503810 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](SC)[N:5]=[C:4]([NH:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=2[O:21][CH3:22])[C:3]=1[C:23](=[O:25])[NH2:24].[Br-].[Cl:27][C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[C:29]=1[CH2:30][Zn+]>O1CCCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[N:7]=[C:6]([CH2:30][C:29]2[C:28]([Cl:27])=[CH:35][CH:34]=[CH:33][C:32]=2[Cl:36])[N:5]=[C:4]([NH:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=2[O:21][CH3:22])[C:3]=1[C:23](=[O:25])[NH2:24]

Participants

5

Reactant 2

HCID 70558051HCID 70558051, compoundHCID 178478100HCID 178478100, compound

Product 1

HCID 70558071HCID 70558071, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
100 °C

Procedure

A suspension of the product of Example 10B (1.1 g, 3.0 mmol), IM (2,6-dichlorobenzyl)zinc(II) bromide in tetrahydrofuran (30 mL, 30 mmol) and tetrakis(triphenylphosphine) palladium(0) (347 mg, 0.3 mmol) in tetrahydrofuran (50 mL) was heated in a sealed tube at 100° C. under nitrogen for 16 hours. The cooled mixture was washed with saturated ammonium chloride solution (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic phase was dried over anhydrous sodium sulfate, filtered, concentrated and purified by flash chromatography on silica gel (200-300 mesh) eluting with 3/1 petroleum ether/ethyl acetate to give the title compound. MS: 476 (M+H+).

Workup

  1. washThe cooled mixture was washed with saturated ammonium chloride solution (50 mL)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography on silica gel (200-300 mesh)
  7. washeluting with 3/1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-16e9ab28688648cd9a102973582101b8
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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