Diisopropylethylamine → HCID 58257812, compound

HRID 2075728Notes

Reaction equation

HRID 2075728 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([C:8]([OH:13])([CH2:11][CH3:12])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=1.[Cl:14][C:15]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]2[C:17](=[CH:18][C:19](I)=[CH:20][CH:21]=2)[N:16]=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]>[Cl:14][C:15]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]2[C:17](=[CH:18][C:19]([S:1][C:2]3[CH:3]=[C:4]([C:8]([OH:13])([CH2:11][CH3:12])[CH2:9][CH3:10])[CH:5]=[CH:6][CH:7]=3)=[CH:20][CH:21]=2)[N:16]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 22036226HCID 22036226, compoundHCID 58257761HCID 58257761, compound

Product 1

HCID 58257812HCID 58257812, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
60 °C

Procedure

10l (900 mg, 4.6 mmol), 2-chloro-7-iodo-4-phenyl-quinoline (10m, 1.6 g, 4.6 mmol), iPr2NEt (1.6 mL, 9.2 mmol), Pd2dba3 (104 mg, 0.1 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (132 mg, 0.2 mmol) were dissolved in 1,4-dioxane (15 mL) and degassed with N2 for 10 minutes. The reaction was heated to 60° C. for 1 hour, and then diluted with saturated aqueous NH4Cl and EtOAc. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (30% EtOAc in hexanes) to give the desired product, 10n.

Workup

  1. customdegassed with N2 for 10 minutes
  2. additiondiluted with saturated aqueous NH4Cl and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-bf3ef940243c43c587d05447d5958831
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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