Cesium carbonate → HCID 67983726, 화합물

HRID 1748220노트

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HRID 1748220 반응식
Br[C:2]1[CH:14]=[CH:13][C:5]2[C:6]([C:9]([O:11][CH3:12])=[O:10])=[N:7][S:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[CH:55]12[NH:62][CH:59]([CH2:60][CH2:61]1)[CH2:58][CH:57]([O:63][CH2:64][C:65]1[C:66]([C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][C:74]=3[O:79][C:80]([F:83])([F:82])[F:81])=[N:67][O:68][C:69]=1[CH:70]1[CH2:72][CH2:71]1)[CH2:56]2>C1(C)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]>[CH:70]1([C:69]2[O:68][N:67]=[C:66]([C:73]3[CH:78]=[CH:77][CH:76]=[CH:75][C:74]=3[O:79][C:80]([F:81])([F:82])[F:83])[C:65]=2[CH2:64][O:63][CH:57]2[CH2:56][CH:55]3[N:62]([C:2]4[CH:14]=[CH:13][C:5]5[C:6]([C:9]([O:11][CH3:12])=[O:10])=[N:7][S:8][C:4]=5[CH:3]=4)[CH:59]([CH2:60][CH2:61]3)[CH2:58]2)[CH2:71][CH2:72]1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 66906285Methyl 6-bromobenzo[d]isothiazole-3-carboxylateHCID 67983256HCID 67983256, 화합물

생성물 1

HCID 67983726HCID 67983726, 화합물

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 7237O-Xylene용매

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온도
120 °C

실험 절차

A microwave vial was charged with methyl 6-bromobenzo[d]isothiazole-3-carboxylate (WO07056582, 85 mg, 0.31 mmol), cesium carbonate (220 mg, 0.68 mmol), tris(dibenzylideneacetone)dipalladium(0) (13 mg, 0.014 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (XPhos) (14 mg, 0.028 mmol), and degassed xylene (1.5 mL). The mixture was degassed for 10 minutes and then 4-((8-azabicyclo[3.2.1]octan-3-yloxy)methyl)-5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazole (I-1H) (115 mg, 0.28 mmol) in xylene (1 mL) was added. The reaction flask was evacuated and backfilled with argon three times and then heated at 120° C. for 12 hours. The reaction mixture was cooled to rt, diluted with ethyl acetate and filtered through a CELITE® pad, the filtrate concentrated, and chromatographed on silica using linear gradient, 20-80%, EtOAc in Hexanes) to give the desired ester as a yellow solid. MS m/z 600.2 (M+1), 622.2. (M+23).

후처리

  1. customdegassed xylene (1.5 mL)
  2. customThe mixture was degassed for 10 minutes
  3. customThe reaction flask was evacuated
  4. temperatureThe reaction mixture was cooled to rt
  5. additiondiluted with ethyl acetate
  6. filtrationfiltered through a CELITE® pad
  7. concentrationthe filtrate concentrated
  8. customchromatographed on silica using linear gradient, 20-80%, EtOAc in Hexanes)

출처 및 근거

ORD 기록
ord-d25f9025b52d4d3bb63aeba0a8d581f7
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150568B2

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