HCID 16040158, compound → HCID 66913780, compound

HRID 2104796Notes

Reaction equation

HRID 2104796 reaction equation
[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:19]=[C:20]([C:24]#[C:25][C:26]3[CH:31]=[CH:30][C:29]([CH2:32][C:33]([OH:35])=[O:34])=[CH:28][CH:27]=3)[CH:21]=[CH:22][CH:23]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:36]([F:39])([F:38])[F:37])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:19]=[C:20]([CH2:24][CH2:25][C:26]3[CH:27]=[CH:28][C:29]([CH2:32][C:33]([OH:35])=[O:34])=[CH:30][CH:31]=3)[CH:21]=[CH:22][CH:23]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:36]([F:37])([F:38])[F:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 16040158HCID 16040158, compound

Product 1

HCID 66913780HCID 66913780, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22609514Ethyl acetate acetateSolvent

Procedure

A solution of [4-({3-[3-benzyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}ethynyl)-phenyl]acetic acid (50 mg, 0.09 mmol), in ethyl acetate:acetic acid (8:1, 4.0 mL) is treated with Pd/C (10%) (3 mg) and placed on a PARR hydrogenator under 40 psi H2 The reaction filtered through celite and concentrated in vacuo. After chromatography (ethyl acetate:hexane, 33:70) the title saturated compound is obtained, 40 mg (80%). MS (ES) m/z 524.1.

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated in vacuo
  3. customAfter chromatography (ethyl acetate:hexane, 33:70) the title saturated compound is obtained

Sources & evidence

ORD record
ord-eef4b8983bcd4196ace57d3d2ecd4c89
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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