HCID 45381859, compound → HCID 45381858, compound

HRID 2176164Notes

Reaction equation

HRID 2176164 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]\[N:10]2[C:18]3[CH:17]=[CH:16][C:15]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:14][C:13]=3[C:12]3[CH2:24][N:25]4[CH2:30][CH2:29][CH:28]([C:11]2=3)[CH2:27][CH2:26]4)=[CH:4][CH:3]=1>CO.[Pt]=O>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[C:18]3[CH:17]=[CH:16][C:15]([O:19][C:20]([F:22])([F:23])[F:21])=[CH:14][C:13]=3[C:12]3[CH2:24][N:25]4[CH2:26][CH2:27][CH:28]([C:11]2=3)[CH2:29][CH2:30]4)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 45381859HCID 45381859, compound

Product 1

HCID 45381858HCID 45381858, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A solution of 6-[(Z)-2-(6-methylpyridin-3-yl)vinyl]-9-(trifluoromethoxy)-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole (65 mg, 0.157 mmol; Example 177) in methanol was treated with platinum oxide under a hydrogen atmosphere (1 atm) at 40° C. for 16 hours to afford the title compound as the major product: 1H NMR (300 MHz, methanol-d4) δ ppm 1.57-1.71 (m, 2H), 1.86-2.00 (m, 2H), 2.40 (s, 3H), 2.89-2.31 (m, 7H), 4.16 (s, 2H), 4.42 (t, J=6 Hz, 2H), 6.93 (ddd, J=9, 2, 1 Hz, 1H), 7.11 (d, J=8 Hz, 1H), 7.18 (d, J=1 Hz, 1H), 7.25 (d, J=9 Hz, 1H), 7.31 (dd, J=8, 2 Hz, 1H), 7.82 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 416 (M+H)+.

Sources & evidence

ORD record
ord-b06b3fc1ffc04f3986d00d0fd8dfea56
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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