Triethylamine → HCID 67111749, 화합물

HRID 1177550노트

반응식

HRID 1177550 반응식
C(N(CC)CC)C.[O:8]1[CH2:13][CH2:12][CH2:11][O:10][CH:9]1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][C:22]3[CH:28]=[C:27](Br)[CH:26]=[CH:25][C:23]=3[N:24]=2)=[C:16]([F:30])[CH:15]=1.C[CH2:32][O:33][C:34](C)=[O:35]>CN(C=O)C.C1COCC1.CO>[O:8]1[CH2:13][CH2:12][CH2:11][O:10][CH:9]1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:21][C:22]3[CH:28]=[C:27]([C:34]([O:33][CH3:32])=[O:35])[CH:26]=[CH:25][C:23]=3[N:24]=2)=[C:16]([F:30])[CH:15]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 671120772-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-6-bromobenzo[d]thiazole

생성물 1

HCID 67111749HCID 67111749, 화합물

시약·촉매·용매 1

HCID 86634690HCID 86634690, 화합물용매

반응 조건

온도
95 °C

실험 절차

Triethylamine (0.32 mL, 2.28 mmol), 1,3-(bis[diphenylphosphino]propane) dichloropalladium(II) (0.051 g, 0.076 mmol), and 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-6-bromobenzo[d]thiazole (0.75 g, 1.90 mmol) were mixed in DMF:THF:MeOH (2:7:2, 11 mL total volume) in a heavy-walled pressure tube. The tube was placed under CO atmosphere (20 psi) and then heated to 95° C. for 16 h. The mixture was cooled to RT and EtOAc (5 mL) was added. The suspension was filtered and the collected solid was washed with EtOAc. The solid obtained was then partitioned between DCM and water, the layers were separated, and the organic layer was dried (MgSO4) and concentrated under vacuum to give methyl 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)benzo[d]thiazole-6-carboxylate as a white solid.

후처리

  1. temperatureThe mixture was cooled to RT
  2. filtrationThe suspension was filtered
  3. washthe collected solid was washed with EtOAc
  4. customThe solid obtained
  5. customwas then partitioned between DCM and water
  6. customthe layers were separated
  7. dry with materialthe organic layer was dried (MgSO4)
  8. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-a7fd57d762c940adb4d23427f774e080
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842685B2

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