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Water → HCID 69085360, 화합물

HRID 594758
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HRID 594758 반응식
N1C=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]2[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]4[S:28][CH:29]=[CH:30][N:31]=4)[CH:22]=3)[C:18](=[O:32])[CH2:17][CH2:16][CH2:15][CH2:14]2)=CC=1.C([Sn](CCCC)(CCCC)C1[N:39]=[CH:40][S:41]C=1)CCC.O.CCOC(C)=O>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[S:28]1[CH:29]=[CH:30][N:31]=[C:27]1[C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][N:19]1[CH:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:4]2[N:39]=[CH:40][S:41][CH:5]=2)[CH2:14][CH2:15][CH2:16][CH2:17][C:18]1=[O:32]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 27632584-(Tri-n-butylstannyl)thiazoleHCID 69084093HCID 69084093, 화합물

생성물 1

HCID 69085360HCID 69085360, 화합물

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매
HCID 8028
Tetrahydrofuran
용매

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온도
75 °C

실험 절차

A mixture of 7-(2-bromophenyl)-1-(3-(thiazol-2-yl)benzyl)azepan-2-one (preparation described in example 450; 50 mg; 0.11 mmol), commercially available 4-(tributylstannyl)thiazole (51 mg; 0.13 mmol), and PdCl2(PPh3)2 (8 mg; 0.011 mmol) in THF (1 ml) was heated to 75° C., under nitrogen, for 18 h. After cooling to rt, water and AcOEt were added. The separated aq. layer was further extracted with AcOEt. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions A): tR=0.84 min.; [M+H]+: 446.14 g/mol.

후처리

  1. temperatureAfter cooling to rt
  2. extractionThe separated aq. layer was further extracted with AcOEt
  3. washThe mixed organic layers were washed with brine
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customSubsequent purification by preparative HPLC
  8. customafforded the target compound

출처 및 근거

ORD 기록
ord-7b0e8e0741134aecbbc1d139c34cbbc1
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242970B2

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