Triethylamine → HCID 70981775, compound

HRID 1468690Notes

Reaction equation

HRID 1468690 reaction equation
Br[C:2]1[S:3][C:4]2[C:10](C3C=CC(Cl)=CC=3)=[C:9]([O:18][CH3:19])[C:8]([CH3:20])=[CH:7][C:5]=2[N:6]=1.[C:21]([CH:23]1[CH2:25][CH2:24]1)#[CH:22].CCN(CC)CC>C1COCC1.[Cu]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]>[CH:23]1([C:21]#[C:22][C:2]2[S:3][C:4]3[CH:10]=[C:9]([O:18][CH3:19])[C:8]([CH3:20])=[CH:7][C:5]=3[N:6]=2)[CH2:25][CH2:24]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 138823CyclopropylacetyleneHCID 70982168HCID 70982168, compound

Product 1

HCID 70981775HCID 70981775, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-bromo-7-(4-chlorophenyl)-6-methoxy-5-methylbenzo[d]thiazole (8C) (188 mg, 0.512 mmol) in THF (3 ml), was added ethynylcyclopropane (0.09 ml, 1.2 mmol), CuI (10 mg, 0.052 mmol), Et3N (0.36 ml, 2.58 mmol) and PdCl2(dppf) (19 mg, 0.026 mmol). The reaction mixture was stirred at 60° C. for 2 hs. The reaction mixture was washed by water, extracted by EtOAc. The organic phase was combined, dried over MgSO4, filtered, concentrated and purified by silica gel column, eluting by 0-50% EtOAc in hexanes.

Workup

  1. washThe reaction mixture was washed by water
  2. extractionextracted by EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel column
  7. washeluting by 0-50% EtOAc in hexanes

Sources & evidence

ORD record
ord-bfd0e06299fc41f886743682a5410d86
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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