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Hydrochloric Acid → HCID 10236524, 화합물

HRID 1836030
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HRID 1836030 반응식
Br[C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:12]=2[CH:13]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>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.CCO>[OH:8][C:6]1[CH:5]=[CH:4][C:3]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:12]=3[CH:13]=2)=[C:2]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=1
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 66827Phenylboronic AcidHCID 10236546HCID 10236546, 화합물

생성물 1

HCID 10236524HCID 10236524, 화합물수율 47.9%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol
용매

실험 절차

Compound 102 (0.2 g, 0.69 mmol) in a solution consisting of Tol/EtOH/2M Na2CO3 aq (5/1/5) was treated with phenylboronic acid (0.12 g, 1.0 mmol) and cat Pd(PPh3)4 and heated to reflux until TLC analysis indicated complete reaction. The reaction was worked up by acidifying with 2 N HCl aq and extracting with EtOAc. The organic layer was washed with saturated NaHCO3 aq, brine, and dried over MgSO4. After filtering and concentrating, the crude material was chromatographed on silica gel (1:9 EtOAc/hexanes to 4:6 EtOAc/hexanes) and then triturated with hexanes to yield 0.10 g of the desired material: Mp=167-170° C.; 1H NMR (DMSO-d6) δ 9.98 (br s, 1 H), 9.07 (br s, 1 H), 7.68 (d, 1 H, J=8.5 Hz), 7.4-7.38 (m, 3 H), 7.26-7.22 (m, 2 H), 7.18 (d, 1H, J=8.7 Hz), 6.90 (dd, 1 H, J=8.5 Hz, 2.5 Hz), 6.72 (d, 1 H, J=2.5 Hz), 6.67 (d, 1 H, J=2.3 Hz), 6.62 (dd, 1 H, J=8.7 Hz, 2.4 Hz), 5.81 (s, 1 H).

후처리

  1. temperatureheated
  2. temperatureto reflux until TLC analysis
  3. customreaction
  4. extractionextracting with EtOAc
  5. washThe organic layer was washed with saturated NaHCO3 aq, brine
  6. dry with materialdried over MgSO4
  7. filtrationAfter filtering
  8. concentrationconcentrating
  9. customthe crude material was chromatographed on silica gel (1:9 EtOAc/hexanes to 4:6 EtOAc/hexanes)
  10. customtriturated with hexanes

출처 및 근거

ORD 기록
ord-c5b2112da7554ee896ba5966dee9a997
출처 데이터셋
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06774248B2

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