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Water → HCID 69084093, 화합물

HRID 594756
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HRID 594756 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[S:23][CH:24]=[CH:25][N:26]=3)[CH:17]=2)[C:13](=[O:27])[CH2:12][CH2:11][CH2:10][CH2:9]1.[N:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1COCC1.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.CCOC(C)=O>[N:28]1[CH:33]=[CH:32][C:31]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH:8]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]4[S:23][CH:24]=[CH:25][N:26]=4)[CH:17]=3)[C:13](=[O:27])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:30][CH:29]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 69082877HCID 69082877, 화합물

생성물 1

HCID 69084093HCID 69084093, 화합물

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

A mixture of 7-(2-bromophenyl)-1-(3-(thiazol-2-yl)benzyl)azepan-2-one (50 mg; 0.11 mmol), commercially available pyridin-4-ylboronic acid (14 mg; 0.11 mmol), and Pd(PPh3)4 (7 mg; 0.006 mmol) in THF (2 ml), and aq. 2 M Na2CO3 (0.2 ml) was heated to 80° C., under nitrogen, for 24 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 7-(2-(pyridin-4-yl)phenyl)-1-(3-(thiazol-2-yl)benzyl)azepan-2-one. LC-MS (conditions A): tR=0.62 min.; [M+H]+: 440.15 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

출처 및 근거

ORD 기록
ord-ee52a88c7f854fc1888ec1300f15e65a
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242970B2

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