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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 1259365
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HRID 1259365 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-8ebe49e6572f4199a17b165266a5e29a
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08466289B2

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