Triphenylphosphine → HCID 86732450, compound

HRID 1776424Notes

Reaction equation

HRID 1776424 reaction equation
[F:1][C:2]1[CH:32]=[C:31](I)[CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[C:17]([O:27][CH3:28])=[CH:16][N:15]=2)=[N:6]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:53]([Si:55]([CH3:58])([CH3:57])[CH3:56])#[CH:54]>C(N(CC)CC)C.C1(/C=C/C(=O)/C=C/C2C=CC=CC=2)C=CC=CC=1.[Pd].[Cu]I>[F:1][C:2]1[CH:32]=[C:31]([C:54]#[C:53][Si:55]([CH3:58])([CH3:57])[CH3:56])[CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:14]2[N:19]=[C:18]([NH:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[C:17]([O:27][CH3:28])=[CH:16][N:15]=2)=[N:6]1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 71553620HCID 71553620, compound

Product 1

HCID 86732450HCID 86732450, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 15673654(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one palladiumCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

144.7 mg of 2-[1-(2-fluoro-4-iodobenzyl)-1H-indazol-3-yl]-5-methoxy-N-(pyridin-4-yl)pyrimidin-4-amine (2-201, 0.262 mmol, 1 eq.), 6.02 mg of (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one-palladium (2:1) (0.01 mmol, 0.04 eq.), 2.0 mg of copper (I) iodide (0.01 mmol, 0.04 eq.), and 13.7 mg of triphenylphosphane (0.052 mmol, 0.2 mmol) were suspended in 2.6 ml of dry N,N-diethylethanamine and purged with nitrogen. Then 3.86 ml of ethynyl(trimethyl)silane (1.57 mmol, 6 eq.) were added and the reaction mixture was stirred at 60° C. for 18 hours. The mixture was concentrated under vacuo. The crude product was used without further purification in step 2.

Workup

  1. custompurged with nitrogen
  2. concentrationThe mixture was concentrated under vacuo
  3. customThe crude product was used without further purification in step 2

Sources & evidence

ORD record
ord-576569c93bdf4bbdbc3bc5dd48991d19
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

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