Diisopropylethylamine → HCID 67091005, compound

HRID 2075705Notes

Reaction equation

HRID 2075705 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:13][N:14]=[C:7]1[C:6](=[O:21])[NH:5]2.[SH:22][C:23]1[CH:24]=[C:25]([C:29]2([C:35]#[N:36])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH:26]=[CH:27][CH:28]=1.CCN(C(C)C)C(C)C.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>CN1C(=O)CCC1.CCOC(C)=O.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:21]=[C:6]1[NH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([S:22][C:23]3[CH:24]=[C:25]([C:29]4([C:35]#[N:36])[CH2:30][CH2:31][O:32][CH2:33][CH2:34]4)[CH:26]=[CH:27][CH:28]=3)[CH:3]=2)[N:8]2[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:13][N:14]=[C:7]12

Participants

9

Reactant 4

HCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 187863864-(3-Mercapto-phenyl)-tetrahydro-pyran-4-carbonitrileHCID 58926503HCID 58926503, compound

Product 1

HCID 67091005HCID 67091005, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

7a (108 mg, 0.32 mmol) and 4-(3-mercapto-phenyl)-tetrahydro-pyran-4-carbonitrile (7b, 86 mg, 0.38 mmol) were dissolved in NMP (3.2 mL) and degassed with N2 for 20 minutes. iPr2NEt (0.12 mL, 0.70 mmol) was added, followed by Pd2dba3 (15 mg, 0.02 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (19 mg, 0.03 mmol). The reaction was sealed and heated overnight at 130° C., and then cooled to room temperature and diluted with EtOAc and water. The organic layer was washed with water and brine, dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (25-100% EtOAc in hexanes, followed by 10% MeOH in EtOAc) to give the desired product, 7c.

Workup

  1. customdegassed with N2 for 20 minutes
  2. customThe reaction was sealed
  3. temperaturecooled to room temperature
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (25-100% EtOAc in hexanes, followed by 10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-9edc254ab581479f8d75e319ab33c8fc
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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