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Sodium Carbonate → HCID 67069923, 화합물

HRID 2390817
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HRID 2390817 반응식
Br[C:2]1[C:3]([C:25]#[N:26])=[C:4]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[CH:16][CH:15]=2)[CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=1.[CH2:27]([O:34][C:35]1[C:40](B(O)O)=[CH:39][CH:38]=[CH:37][N:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C([O-])([O-])=O.[Na+].[Na+]>CO.C(Cl)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>[CH2:27]([O:34][C:35]1[C:40]([C:2]2[C:3]([C:25]#[N:26])=[C:4]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([NH:20][S:21]([CH3:24])(=[O:22])=[O:23])=[CH:18][CH:19]=3)[CH:5]=[C:6]([C:8]([CH3:10])([CH3:11])[CH3:9])[CH:7]=2)=[CH:39][CH:38]=[CH:37][N:36]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 44755161B-[2-(Phenylmethoxy)-3-pyridinyl]boronic acidHCID 67070067HCID 67070067, 화합물

생성물 1

HCID 67069923HCID 67069923, 화합물수율 64.1%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매
HCID 887
Methanol
용매
HCID 6344Dichloromethane용매

실험 절차

step 3—A sealed tube containing 94 (0.290 g, 0.67 mmol), 2-benzyloxy-3-pyridine boronic acid (0.184 g, 0.80 mmol, 141), Pd(PPh3)4 (0.220 g, 0.07 mmol) and Na2CO3 (0.609 g, 2.01 mmol) in MeOH (9 mL) and DCM (3 mL) was irradiated in a microwave reactor at 125° C. for 30 min. The organic volatiles were removed under reduced pressure. The residue was partitioned between DCM and water then the aqueous layer was further extracted with DCM. The combined extracts were washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with 20% EtOAc/hexanes to afford 0.230 g (64%) of N-{4-[3-(2-benzyloxy-pyridin-3-yl)-5-tert-butyl-2-cyano-phenylethynyl]phenyl}-methanesulfonamide (96) as a light brown solid.

후처리

  1. customstep 3—A sealed tube
  2. customwas irradiated in a microwave reactor at 125° C. for 30 min
  3. customThe organic volatiles were removed under reduced pressure
  4. customThe residue was partitioned between DCM and water
  5. extractionthe aqueous layer was further extracted with DCM
  6. washThe combined extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude residue was purified by SiO2 chromatography
  11. washeluting with 20% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-ca5ef61ce15b4a16bcbaa1c11698f17c
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08273773B2

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