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Potassium Carbonate → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-morpholinopyridin-4-yl)benzo[d]thiazol-6-yl)acetate

HRID 879428
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HRID 879428 반응식
[C:1]([O:5][C@@H:6]([C:12]1[C:33]([CH3:34])=[CH:32][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:30][CH2:29]N(C)[CH2:27][CH2:26]4)[CH:20]=3)[S:18][C:14]=2[C:13]=1OS(C(F)(F)F)(=O)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[Cl:43][C:44]1[CH:49]=[CH:48][C:47](B(O)O)=[CH:46][CH:45]=1.C(=O)([O-])[O-:54].[K+].[K+]>CC(OC)(C)C.COC1C=CC=C(OC)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1.C1C=[C-]C(CCN)=CC=1.Cl[Pd+].C(COC)OC.C(OCC)(=O)C>[C:1]([O:5][C@@H:6]([C:12]1[C:33]([CH3:34])=[CH:32][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH2:26][CH2:27][O:54][CH2:29][CH2:30]4)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:47]1[CH:48]=[CH:49][C:44]([Cl:43])=[CH:45][CH:46]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acid2회HCID 131732631(S)-ethyl 2-tert-butoxy-2-(5-methyl-2-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)acetate

생성물 1

HCID 86700235(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-morpholinopyridin-4-yl)benzo[d]thiazol-6-yl)acetate

시약·촉매·용매 3

HCID 71311105
SPhos Palladacycle
촉매
2회
HCID 80711,2-Dimethoxyethane용매
HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

A mixture of (S)-ethyl 2-tert-butoxy-2-(5-methyl-2-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)-7-(trifluoromethylsulfonyloxy)benzo[d]thiazol-6-yl)acetate (20 mg, 0.0324 mmol), 4-chlorophenyboronic acid (10 mg, 0.063 mmol), SPhos precatalyst (3.3 mg, 0.0049 mmol) and powdered potassium carbonate (18 mg, 0.129 mmol) in anhydrous dimethoxyethane (0.75 mL) was sparged with nitrogen for 5 minutes, then heated in microwave at 120° C. for 1.5 h. Added more 4-chlorophenyboronic acid and SPhos precatalyst (3.3 mg, 0.0049 mmol) and continued reaction. Reaction mixture was diluted with ethyl acetate, washed with brine, dried (MgSO4), filtered, concentrated and purified by CombiFlash (0 to 40% EtOAc/Hex) to give product. LCMS-ESI+: calc'd for C31H35ClN3O4S: 580.2 (M+H+); Found: 580.3 (M+H+).

후처리

  1. customwas sparged with nitrogen for 5 minutes
  2. customreaction
  3. customReaction mixture
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by CombiFlash (0 to 40% EtOAc/Hex)
  9. customto give product

출처 및 근거

ORD 기록
ord-a5f6f03f816147c7bdc907438768fd53
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08987250B2

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