Potassium Phosphate, Tribasic → 1-Benzyl-7-(2-fluoro-4-trimethylsilanyl-phenylamino)-6-methyl-8-nitro-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-one

HRID 1259365Notes

Reaction equation

HRID 1259365 reaction equation
[CH2:1]([N:8]1[C:12]2=[C:13]([N+:27]([O-:29])=[O:28])[C:14](OS(C(F)(F)F)(=O)=O)=[C:15]([CH3:18])[C:16](=[O:17])[N:11]2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:30][C:31]1[CH:36]=[C:35]([Si:37]([CH3:40])([CH3:39])[CH3:38])[CH:34]=[CH:33][C:32]=1[NH2:41].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([N:8]1[C:12]2=[C:13]([N+:27]([O-:29])=[O:28])[C:14]([NH:41][C:32]3[CH:33]=[CH:34][C:35]([Si:37]([CH3:39])([CH3:38])[CH3:40])=[CH:36][C:31]=3[F:30])=[C:15]([CH3:18])[C:16](=[O:17])[N:11]2[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 58380548HCID 58380548, compoundHCID 595965992-Fluoro-4-(trimethylsilyl)aniline

Product 1

HCID 671936841-Benzyl-7-(2-fluoro-4-trimethylsilanyl-phenylamino)-6-methyl-8-nitro-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-oneYield 85.7%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

Trifluoro-methanesulfonic acid 1-benzyl-6-methyl-8-nitro-5-oxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyridin-7-yl ester (I-1e: 500 mg, 0.001 mol) in toluene (15 mL) was reacted with 2-fluoro-4-trimethylsilanyl-phenylamine (221 mg, 0.001 mol) in the presence of Pd2(dba)3 (63.3 mg, 0.0001 mol), xantphos (40 mg, 0.0001 mol) and K3PO4 (367 mg, 0.002 mol) and the reaction mixture was heated to reflux for 1 hour. Reaction workup yields the crude product which was purified by column chromatography on silica gel (40% ethylacetate in hexane) to afford 400 mg of the product (74.48% yield).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. customReaction workup
  4. customyields the crude product which
  5. customwas purified by column chromatography on silica gel (40% ethylacetate in hexane)

Sources & evidence

ORD record
ord-8ebe49e6572f4199a17b165266a5e29a
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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