HCID 117940136, compound → HCID 117939997, compound

HRID 62254Notes

Reaction equation

HRID 62254 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5](/[CH:6]=[C:7]2/[C:8](=[O:24])[C:9]3[C:14]([CH2:15]/2)=[CH:13][C:12]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[C:11]([O:22][CH3:23])[CH:10]=3)=[CH:4][C:3]=1[C:27]([F:30])([F:29])[F:28]>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][CH:7]2[CH2:15][C:14]3[C:9](=[CH:10][C:11]([O:22][CH3:23])=[C:12]([N:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)[CH:13]=3)[C:8]2=[O:24])=[CH:4][C:3]=1[C:27]([F:30])([F:28])[F:29]

Participants

4

Reactant 1

HCID 117940136HCID 117940136, compound

Product 1

HCID 117939997HCID 117939997, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The 88 (65 mg, 0.148 mmol) was dissolved in ethyl acetate 50 mL, Pd/C 15 mg added, and the reaction stirred under hydrogen balloon for 6 h, then filtered through celite bed and washed with excess methanol. The organic layer was concentrated to get the crude compound 89. The crude was purified by flash chromatography using 100-200 mesh silica gel. The compound 89 was eluted at 25% ethyl acetate in hexane as half white coloured solid compound 2-(4-chloro-3-(trifluoromethyl)benzyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 89. 1HNMR (400 MHz, CDCl3) δ ppm 7.55 (d, 1H), 7.41 (d, 1H), 7.34 (dd, 1H), 7.17 (s, 1H), 6.81 (s, 1H), 3.87 (m, 7H), 3.33 (dd, 1H), 3.17 (m, 4H), 3.06 (m, 1H), 2.93 (m, 1H), 2.66 (m, 2H); MS (ESI) m/z 439.9 (M+H).

Workup

  1. filtrationfiltered through celite bed
  2. washwashed with excess methanol
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-f5a042c9e7c5475c8a5d46507f0de7f9
Source dataset
uspto-grants-2016_09
Patent number
US09446047B2

Reaction notes

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