Sodium Carbonate → HCID 86687961, 화합물

HRID 509346

반응식

HRID 509346 반응식
Cl.[F:2][C:3]([F:23])([F:22])[C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([C:12]2[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][N:13]=2)[NH2:11])=[CH:6][CH:5]=1.[C:24](=[O:27])([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.Br[C:73]1[CH:81]=[C:80]2[C:76]([CH2:77][NH:78][C:79]2=[O:82])=[CH:75][CH:74]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[O:82]=[C:79]1[C:80]2[C:76](=[CH:75][CH:74]=[C:73]([C:24]([NH:11][C@@H:10]([C:7]3[CH:6]=[CH:5][C:4]([C:3]([F:22])([F:2])[F:23])=[CH:9][CH:8]=3)[C:12]3[C:17]([C:18]([F:21])([F:19])[F:20])=[CH:16][CH:15]=[CH:14][N:13]=3)=[O:27])[CH:81]=2)[CH2:77][NH:78]1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 222209196-Bromo-2,3-dihydro-1H-isoindol-1-oneHCID 86687962(S)-(4-(Trifluoromethyl)phenyl)(3-(trifluoromethyl)pyridin-2-yl)methanamine Hydrochloride2회

생성물 1

HCID 86687961HCID 86687961, 화합물

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

실험 절차

To a 25 mL round bottom flask containing (S)-(4-(trifluoromethyl)-phenyl)(3-(trifluoromethyl)pyridin-2-yl)methanamine hydrochloride (Intermediate 1) (120 mg, 0.336 mmol) was added toluene (3 mL). The resulting mixture was stirred at rt for 2 min. At this time, sodium carbonate (143 mg, 1.346 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (3.89 mg, 6.73 mol), palladium (II) acetate (1.5 mg, 6.7 mol) and 6-bromo-2,3-dihydro-isoindol-1-one (71.3 mg, 0.336 mmol) were added to the flask. The reaction vessel was flushed with argon and then left under 1.0 atm of carbon monoxide gas (from a lecture bottle, in hood). The flask was heated to 85° C. overnight, filtered though Celite® brand filter agent, and eluted with EtOAc. Purification by reverse phase HPLC, and concentration of the containing fractions gave (S)-3-oxo-N-((4-(trifluoromethyl)-phenyl)(3-(trifluoromethyl)pyridin-2-yl)methyl)isoindoline-5-carboxamide as a yellow foamy solid. 1H NMR (300 MHz, CDCl3): δ ppm 8.92 (d, J=4.5 Hz, 1H), 8.40 (d, J=7.7 Hz, 1H), 7.60-7.56 (m, 5H), 7.46-7.48 (m, 2H), 6.90 (d, J=7.6 Hz, 1H), 4.54 (s, 2H). MS (ESI pos. ion) m/z: 480.1 (M+H).

후처리

  1. customThe reaction vessel was flushed with argon
  2. waitleft under 1.0 atm of carbon monoxide gas (from a lecture bottle
  3. temperatureThe flask was heated to 85° C. overnight
  4. filtrationfiltered though Celite® brand
  5. filtrationfilter agent
  6. washeluted with EtOAc
  7. customPurification by reverse phase HPLC, and concentration of the containing fractions

출처 및 근거

ORD 기록
ord-e7818bdf74ff43969760c74e84ca7bd3
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096527B2

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