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Sodium Carbonate → Trifluoroacetic acid

HRID 931787
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인쇄 미리보기

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HRID 931787 반응식
[C:1]([O:7][CH2:8][C@@H:9]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[C:10]1[C:11]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15](OS([C:25]([F:28])([F:27])[F:26])(=O)=O)[CH:14]=[CH:13]2)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[Cl:41][C:42]1[CH:47]=[CH:46][C:45](B(O)O)=[CH:44][CH:43]=1.[C:51]([O-])([O-:53])=[O:52].[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:7][CH2:8][C@H:9]([C:10]1[C:11]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([C:45]1[CH:46]=[CH:47][C:42]([Cl:41])=[CH:43][CH:44]=1)[CH:14]=[CH:13]2)[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])(=[O:6])[C:2]([CH3:3])([CH3:5])[CH3:4].[C:51]([OH:53])([C:25]([F:26])([F:27])[F:28])=[O:52]
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참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 86691982(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate2회

생성물 2

HCID 6422Trifluoroacetic acid수율 328.9%HCID 66631695HCID 66631695, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
90 °C

실험 절차

Pd(PPh3)4 (4.6 mg, 0.004 mmol) was added to a mixture (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate (compound of Example 26) (25 mg, 0.04 mmol), 4-chlorophenylboronic acid (13 mg, 0.08 mmol), Na2CO3 (0.14 mL 1 M in water, 0.14 mmol) in 1,2-dimethoxyethane (2 mL). The reaction mixture was flushed with nitrogen, heated at 90° C. for 16 hours, and then the volatile component was removed in vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by HPLC to provide the desired product as a TFA salt (15 mg, 55%). LCMS-ESI+ (m/z): 564.3, 566.3, 568.3 (M+H)+.

후처리

  1. customThe reaction mixture was flushed with nitrogen
  2. customthe volatile component was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  4. washwashed with NaHCO3 solution, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe obtained residue was purified by HPLC

출처 및 근거

ORD 기록
ord-192506ec3b024ba49cb1079a01a0a774
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09296758B2

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