Triethylamine → HCID 9797871, compound

HRID 428725Notes

Reaction equation

HRID 428725 reaction equation
N1C=CC=C1/C=C1\C(=O)N(C#C)C2C\1=C[C:13]([Si:16]([CH3:19])([CH3:18])[CH3:17])=[CH:12]C=2.Br[C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][C:28](=[O:33])/[C:27]/2=[CH:34]\[C:35]1[NH:36][CH:37]=[CH:38][C:39]=1[O:40][CH3:41].C[Si](C#C)(C)C.C(N(CC)CC)C>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CN(C=O)C>[CH3:41][O:40][C:39]1[CH:38]=[CH:37][NH:36][C:35]=1/[CH:34]=[C:27]1\[C:28](=[O:33])[NH:29][C:30]2[C:26]\1=[CH:25][C:24]([C:12]#[C:13][Si:16]([CH3:19])([CH3:18])[CH3:17])=[CH:32][CH:31]=2

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 9797091HCID 9797091, compoundHCID 86757574HCID 86757574, compound

Product 1

HCID 9797871HCID 9797871, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

This compound was prepared in a manner analogous to the preparation of (Z)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-5-(trimethylsilyl)-ethynyl-2H-indol-2-one in Example 81 above. In this example, (Z)-5-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (740 mg, 2.32 mmol) (from Example 91) was coupled with (trimethylsilyl)acetylene (640 mg, 6.52 mmol) (Aldrich) using CuI (40 mg, 0.21 mmol) (Aldrich) and (Ph3P)2PdCl2 (90 mg, 0.13 mmol) (Aldrich) as catalyst in 10 mL DMF and 10 mL triethylamine at 70° C. for 22 hours to give (Z)-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-5-(trimethylsilyl)ethynyl-2H-indol-2-one. (Yield 410 mg, 52%).

Sources & evidence

ORD record
ord-42751941538547a1a5c4d345d65b61fe
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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