Trimethylsilylacetylene → HCID 59543128, compound

HRID 1971002Notes

Reaction equation

HRID 1971002 reaction equation
[CH:1]1([C@@H:4]([NH:9][C:10]2[C:22]3[C:21]4[CH:20]=[CH:19][C:18](I)=[CH:17][C:16]=4[NH:15][C:14]=3[C:13]([C:24]([NH2:26])=[O:25])=[CH:12][N:11]=2)[C:5]([F:8])([F:7])[F:6])[CH2:3][CH2:2]1.[Si:27]([C:31]#[CH:32])([CH3:30])([CH3:29])[CH3:28]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH:1]1([C@@H:4]([NH:9][C:10]2[C:22]3[C:21]4[CH:20]=[CH:19][C:18]([C:32]#[C:31][Si:27]([CH3:30])([CH3:29])[CH3:28])=[CH:17][C:16]=4[NH:15][C:14]=3[C:13]([C:24]([NH2:26])=[O:25])=[CH:12][N:11]=2)[C:5]([F:8])([F:7])[F:6])[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 59543146HCID 59543146, compound

Product 1

HCID 59543128HCID 59543128, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-{[(1R)-1-Cyclopropyl-2,2,2-trifluoroethyl]amino}-7-iodo-5H-pyrido[4,3-b]indole-4-carboxamide (0.19 g, 0.40 mmol), TMS acetylene (0.12 g, 1.2 mmol), Pd(PPh3)4 (0.047 g, 0.040 mmol), CuI (0.015 g, 0.081 mmol), and TEA (0.082 g, 0.81 mmol) in DMF (4 mL) was purged with nitrogen for 5 min, heated to 50° C. overnight, and cooled to room temperature. The mixture was diluted with EtOAc, washed with water and brine, dried (sodium sulfate), concentrated, and purified by flash chromatography to afford the title compound.

Workup

  1. customwas purged with nitrogen for 5 min
  2. temperaturecooled to room temperature
  3. additionThe mixture was diluted with EtOAc
  4. washwashed with water and brine
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-783585b2d7b24bbfafad712eb7ccf288
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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