2-Bromothiazole → HCID 58257814, compound

HRID 2075722Notes

Reaction equation

HRID 2075722 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.CCN(C(C)C)C(C)C.[C:16]1([C:22]2[N:26]3[C:27]4[C:32]([CH:33]=[CH:34][C:25]3=[N:24][N:23]=2)=[CH:31][C:30]([SH:35])=[CH:29][CH:28]=4)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.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]>[C:16]1([C:22]2[N:26]3[C:27]4[C:32]([CH:33]=[CH:34][C:25]3=[N:24][N:23]=2)=[CH:31][C:30]([S:35][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)=[CH:29][CH:28]=4)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 764302-BromothiazoleHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 58257767HCID 58257767, compound

Product 1

HCID 58257814HCID 58257814, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

To 2-Bromothiazole (0.27 mL, 3.0 mmol) in 1,4-dioxane (20 mL) was added iPr2NEt (0.96 mL, 5.5 mmol), and the reaction was degassed with N2 for 10 minutes. 10e (765 mg, 2.8 mmol) was added, followed by Pd2dba3 (63 mg, 0.07 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (81 mg, 0.14 mmol). The reaction was sealed and heated overnight at 80° C., and then cooled to room temperature and concentrated. The residue was diluted with EtOAc and water, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the crude material was purified by silica gel chromatography (60-100% EtOAc in hexanes) to give the desired product, 10f.

Workup

  1. customthe reaction was degassed with N2 for 10 minutes
  2. customThe reaction was sealed
  3. temperaturecooled to room temperature
  4. concentrationconcentrated
  5. additionThe residue was diluted with EtOAc and water
  6. extractionthe aqueous layer was extracted with EtOAc
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe crude material was purified by silica gel chromatography (60-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d249255d9c2c4344a9c4301419ed1c81
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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