Diazomethane → HCID 86680419, compound

HRID 1023175Notes

Reaction equation

HRID 1023175 reaction equation
[F:1][CH:2]([F:38])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:15]=[C:14](/[CH:16]=[CH:17]/[C:18]3[CH:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[N:24]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:23](=[O:36])[CH:22]=[CH:21]4)[O:13][N:12]=2)=[CH:6][C:5]=1[CH3:37].[N+](=[CH2:41])=[N-]>C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:38][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:15]=[C:14]([C@@H:16]3[CH2:41][C@H:17]3[C:18]3[CH:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[N:24]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[C:23](=[O:36])[CH:22]=[CH:21]4)[O:13][N:12]=2)=[CH:6][C:5]=1[CH3:37]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 86680420HCID 86680420, compound

Product 1

HCID 86680419HCID 86680419, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of (E)-6-(2-(3-((4-(difluoromethoxy)-3-methylphenyl)amino)-1,2,4-oxadiazol-5-yl)vinyl)-1-((2-(trimethylsilyl)ethoxy)methyl)quinolin-2(1H)-one (65 mg, 0.120 mmol) in diethylether (20 mL) were added palladium (II) acetate (2.70 mg, 0.012 mmol) and a diazomethane solution [prepared from N-nitroso-N-methylurea (62.0 mg, 0.601 mmol) and KOH (33.7 mg, 0.61 mmol)]. The reaction was stirred at room temperature overnight, The reaction mixture was filtered through celite and concentrated to give trans-6-(2-(3-((4-(difluoromethoxy)-3-methylphenyl)amino)-1,2,4-oxadiazol-5-yl)cyclopropyl)-1-((2-(trimethylsilyl)ethoxy)methyl)quinolin-2(1H)-one (45 mg, 67%). LCMS, RT 2.25 min; LCMS (ES-API), m/z 555.

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-1b468d9cc4c348e79b39e60a89aeb356
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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