Dichloromethane → (S)-ethyl 2-(tert-butoxy)-2-(7-(4-chlorophenyl)-2-(1,2-dimethyl-1H-benzo[d]imidazol-6-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

HRID 879530노트

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HRID 879530 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH3:10])[N:7]([CH3:11])[C:6]=2[CH:12]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C(Cl)Cl.CC([O-])=O.[K+].Br[C:40]1[S:41][C:42]2[C:48]([C:49]3[CH:54]=[CH:53][C:52]([Cl:55])=[CH:51][CH:50]=3)=[C:47]([C@H:56]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])[C:57]([O:59][CH2:60][CH3:61])=[O:58])[C:46]([CH3:67])=[CH:45][C:43]=2[N:44]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].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:63]([O:62][C@@H:56]([C:47]1[C:46]([CH3:67])=[CH:45][C:43]2[N:44]=[C:40]([C:2]3[CH:3]=[CH:4][C:5]4[N:9]=[C:8]([CH3:10])[N:7]([CH3:11])[C:6]=4[CH:12]=3)[S:41][C:42]=2[C:48]=1[C:49]1[CH:50]=[CH:51][C:52]([Cl:55])=[CH:53][CH:54]=1)[C:57]([O:59][CH2:60][CH3:61])=[O:58])([CH3:64])([CH3:65])[CH3:66]

참가 물질

11

반응물 6

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 581095096-bromo-1,2-dimethyl-1H-benzo[d]imidazoleHCID 86700141(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

생성물 1

HCID 86700350(S)-ethyl 2-(tert-butoxy)-2-(7-(4-chlorophenyl)-2-(1,2-dimethyl-1H-benzo[d]imidazol-6-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

시약·촉매·용매 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

A microwave vial was charged with 6-bromo-1,2-dimethyl-1H-benzo[d]imidazole (150 mg, 0.67 mmol), Bis(pinacolato)diboron (189 mg, 0.74 mmol), PdCl2(dppf).CH2Cl2 (55 mg, 0.07 mmol), then KOAc (221 mg, 2.25 mmol). The vial was flushed with argon, diluted with dioxane (3 mL), sealed, then heated to 100° C. for 45 minutes. The reaction mixture was allowed to cool to room temperature and then a portion of this cooled solution (1.0 mL, 0.22 mmol) was added to a vial that was charged with (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (55 mg, 0.10 mmol) and Pd(PPh3)4 (12 mg, 0.01 mmol). The mixture was diluted with dioxane (1.5 mL) and to this was added 2M aqueous K2CO3 (0.21 mL, 0.42 mmol). The vial was sealed, heated to 100° C. for 1 hour, and then allowed to cool to room temperature. The mixture was diluted with EtOAc, dried over Na2SO4, filtered through a small pad of silica gel, and concentrated in vacuo to afford the desired product. LCMS-ESI+: calc'd C31H33ClN3O3S: 562.2 (M+H+); Found: 562.3 (M+H+).

후처리

  1. customThe vial was flushed with argon
  2. additiondiluted with dioxane (3 mL)
  3. customsealed
  4. temperatureto cool to room temperature
  5. customThe vial was sealed
  6. temperatureheated to 100° C. for 1 hour
  7. temperatureto cool to room temperature
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered through a small pad of silica gel
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4aae3159e68643c1bc313ad78441e03a
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987250B2

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