HCID 58036793, compound → HCID 58036792, compound

HRID 1028359Notes

Reaction equation

HRID 1028359 reaction equation
[C:1]1([P:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[NH:17][CH:16]([CH3:19])[CH:15]=[CH:14]3)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.CCOC(C)=O.[Pd]>[C:20]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[NH:17][CH:16]([CH3:19])[CH2:15][CH2:14]3)=[O:8])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 1

HCID 58036793HCID 58036793, compound

Product 1

HCID 58036792HCID 58036792, compoundYield 100.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 8-diphenylphosphinoyl-2-methyl-1,2-dihydroquinoline (5) (11 g, 32 mmol) and Pd/C (1.1 g, 10 wt %) in MeOH (40 mL) was stirred under H2 at 145 psi pressure for 16 hours. The mixture was then diluted with EtOAc (200 mL) and filtered over celite (˜25 mL). The filtrate was then evaporated to give compound 6 as a yellow oil (11.2 g, quantitative). 1H NMR (400.13 MHz, CDCl3) δ 7.7-7.6 (m, 4H, Ph-H), 7.6-7.5 (m, 2H, Ph-H), 7.5-7.4 (m, 4H, Ph-H), 7.03 (d, 1H, J=7.2 Hz, C5—H), 6.87 (bs, 1H, N1—H), 6.58 (dd, 1H, J=14.0, 7.2 Hz, C7—H), 6.39 (ddd, 1H, J=10.4, 7.2, 2.8 Hz, C6—H), 3.5-3.4 (m, 1H, C2—H), 2.8-2.7 (m, 2H, C4—H), 1.9-1.8 (m, 1H, C3a—H), 1.6-1.4 (m, 1H, C3b—H), 1.13 (d, 3H, J=6.4 Hz, C1′—CH3) ppm; 13C NMR (100.61 MHz, CDCl3) δ 148.9, 132.0 (d, J=11.1 Hz), 131.5, 131.0 (d, J=10.1 Hz), 130.7 (d, J=10.1 Hz), 130.6 (d, J=10.1 Hz), 130.4 (d, J=6.1 Hz), 130.3 (d, J=6.1 H), 130.1 (d, J=11.1 Hz), 127.0 (d, J=13.1 Hz), 126.9 (d, J=12.1 Hz), 120.4 (d, J=8.1 Hz), 112.5 (d, J=14.1 Hz), 107.9, 106.9, 45.4, 27.4, 25.5, 20.9 ppm; 31P NMR (161.97 MHz, CDCl3) δ 36.4 ppm.

Workup

  1. filtrationfiltered over celite (˜25 mL)
  2. customThe filtrate was then evaporated

Sources & evidence

ORD record
ord-c9203be8e2ff415c8245694d0360848c
Source dataset
uspto-grants-2014_05
Patent number
US08735583B2

Reaction notes

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