(5S,6S,9R)-5-azido-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine → 5H-Cyclohepta[b]pyridin-5-amine, 6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-9-[[tris(1-methylethyl)silyl]oxy]-, (5S,6S,9R)-

HRID 1879383Notes

Reaction equation

HRID 1879383 reaction equation
[N:1]([C@@H:4]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[C@H:8]([O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[CH2:7][CH2:6][C@H:5]1[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=1[F:33])=[N+]=[N-]>C(O)C.[Pd]>[F:33][C:27]1[C:28]([F:32])=[CH:29][CH:30]=[CH:31][C:26]=1[C@@H:5]1[CH2:6][CH2:7][C@@H:8]([O:15][Si:16]([CH:20]([CH3:22])[CH3:21])([CH:23]([CH3:25])[CH3:24])[CH:17]([CH3:18])[CH3:19])[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:14]2[C@H:4]1[NH2:1]

Participants

4

Reactant 1

HCID 71533837(5S,6S,9R)-5-azido-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine2×

Product 1

HCID 671158635H-Cyclohepta[b]pyridin-5-amine, 6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-9-[[tris(1-methylethyl)silyl]oxy]-, (5S,6S,9R)-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (5S,6S,9R)-5-azido-6-(2,3-difluorophenyl)-9-(triisopropylsilyloxy)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine (598 mg, 1.265 mmol)(intermediate 9) and palladium (10% on activated carbon) (0.504 mg, 0.474 μmol) in ethanol (25 ml) was stirred under hydrogen (1 atm) for 2.5 h. LCMS indicated that the desired compound was formed, stirring was continued. After 5 h, the mixture was filtered, washed thoroughly with ethanol, and then concentrated to give 21 (525 mg, 93%) as a colorless oil: MS(ESI)[M+H+]=447.3.

Sources & evidence

ORD record
ord-f84263a287e748c9bb11fa77ea57ca16
Source dataset
uspto-grants-2012_11
Patent number
US08314117B2

Reaction notes

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