Diisopropylamine → HCID 67979656, compound

HRID 1770917Notes

Reaction equation

HRID 1770917 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[Cl:9].C[Si](C)(C)[C:12]#[C:13][CH3:14].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(NC(C)C)(C)C>[Cu](I)I.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.CN(C=O)C>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:12]#[C:13][CH3:14])[C:3]=1[Cl:9]

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 803631-(Trimethylsilyl)prop-1-yneHCID 2724141Tetrabutylammonium FluorideHCID 140296611,3-Dibromo-2-chlorobenzene

Product 1

HCID 67979656HCID 67979656, compoundYield 22%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418807HCID 178418807, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a microwave vial were added 1,3-dibromo-2-chlorobenzene (780 mg, 2.89 mmol), trimethyl(prop-1-ynyl)silane (0.645 mL, 4.33 mmol), copper iodide (28 mg, 0.14 mmol), PdCl2(dppf) CH2Cl2 (118 mg, 0.14 mmol), tetrabutylammonium fluoride (1 M in THF, 8.66 mL, 8.66 mmol), diisopropylamine (1.23 mL, 8.66 mmol) and anhydrous DMF (5 mL). The vial was capped and purged with argon and the mixture was irradiated at 100° C. for 1 h in a microwave reactor. The mixture was diluted with water and extracted with DCM three times, dried through a phase separator and concentrated in vacuo. The product was purified by flash chromatography (100% heptanes as eluent) to give 146 mg (22% yield) of the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.13 (s, 3H) 7.24 (t, J=7.88 Hz, 1H) 7.53 (dd, J=7.57, 1.26 Hz, 1H) 7.74 (dd, J=8.04, 1.42 Hz, 1H); MS (CI) m/z 231 [M+H]

Workup

  1. customThe vial was capped
  2. custompurged with argon
  3. customthe mixture was irradiated at 100° C. for 1 h in a microwave reactor
  4. additionThe mixture was diluted with water
  5. extractionextracted with DCM three times
  6. customdried through a phase separator
  7. concentrationconcentrated in vacuo
  8. customThe product was purified by flash chromatography (100% heptanes as eluent)

Sources & evidence

ORD record
ord-3fc61726561e42c68642497b515d852d
Source dataset
uspto-grants-2016_02
Patent number
US09248129B2

Reaction notes

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