Diisopropylethylamine → HCID 58257754, compound

HRID 2075671Notes

Reaction equation

HRID 2075671 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH2:12][CH2:13][N:14]=[C:7]1[CH:6]=[CH:5]2.[SH:15][C:16]1[CH:17]=[C:18]([C:22]2([OH:28])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:19]=[CH:20][CH:21]=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>O1CCOCC1.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]>[CH2:12]1[N:8]2[C:9]3[C:4]([CH:5]=[CH:6][C:7]2=[N:14][CH2:13]1)=[CH:3][C:2]([S:15][C:16]1[CH:17]=[C:18]([C:22]2([OH:28])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH:19]=[CH:20][CH:21]=1)=[CH:11][CH:10]=3

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 58257766HCID 58257766, compoundHCID 582578014-(3-Mercapto-phenyl)-tetrahydro-pyran-4-ol

Product 1

HCID 58257754HCID 58257754, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

2a (175 mg, 0.59 mmol) and 4-(3-mercapto-phenyl)-tetrahydro-pyran-4-ol (2b, 150 mg, 0.71 mmol) were combined in 1,4-dioxane (6 mL) and degassed with N2 for 10 minutes. iPr2NEt (0.33 mL, 1.8 mmol) was added, followed by Pd2dba3 (14 mg, 0.02 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (16 mg, 0.03 mmol). The mixture was degassed with N2 for an additional 10 minutes, and then heated to 80° C. for 24 hours. The reaction was cooled to room temperature, concentrated, and purified by silica gel chromatography (0-20% MeOH in EtOAc) to give the desired product, 2c.

Workup

  1. customdegassed with N2 for 10 minutes
  2. customThe mixture was degassed with N2 for an additional 10 minutes
  3. temperatureThe reaction was cooled to room temperature
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (0-20% MeOH in EtOAc)

Sources & evidence

ORD record
ord-179d62c4a946496abaf06f0dd79a895c
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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