Trimethylsilylacetylene → HCID 68380191, compound

HRID 331168Notes

Reaction equation

HRID 331168 reaction equation
[F:1][C:2]1([F:21])[C:8]([CH3:10])([CH3:9])[O:7][CH2:6][C:5]([NH2:11])=[N:4][C@@:3]1([C:13]1[CH:18]=[C:17](I)[CH:16]=[CH:15][C:14]=1[F:20])[CH3:12].[C:22]([Si:24]([CH3:27])([CH3:26])[CH3:25])#[CH:23]>[Pd]>[F:1][C:2]1([F:21])[C:8]([CH3:10])([CH3:9])[O:7][CH2:6][C:5]([NH2:11])=[N:4][C@@:3]1([C:13]1[CH:18]=[C:17]([C:23]#[C:22][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:16]=[CH:15][C:14]=1[F:20])[CH3:12]

Participants

4

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 68380322HCID 68380322, compound

Product 1

HCID 68380191HCID 68380191, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a manner analogous to that described in Example 9a), palladium-catalyzed coupling of (R)-6,6-Difluoro-5-(2-fluoro-5-iodo-phenyl)-5,7,7-trimethyl-2,5,6,7-tetrahydro-[1,4]oxazepin-3-ylamine (485 mg, 1.18 mmol) with ethynyltrimethylsilane yielded the title compound (350 mg, 78% yield) as a yellow oil. MS (ISP): m/z=383.2 [M+H]+.

Sources & evidence

ORD record
ord-fdad7c930609445d88708050f2dd2d1b
Source dataset
uspto-grants-2014_11
Patent number
US08877744B2

Reaction notes

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