Triphenylphosphine → 1-(6,7-Di-vinyl-2-benzothiazolyl)-3-ethylurea

HRID 9124

반응식

HRID 9124 반응식
Br[C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[C:3]=1S(C(F)(F)F)(=O)=O.[Cl-].[Li+].[C:26]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:27]=1.[CH:45]([Sn](C=C)(C=C)C=C)=[CH2:46].[Sn]>CO.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>[CH:26]([C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([NH:9][C:10]([NH:12][CH2:13][CH3:14])=[O:11])[S:8][C:4]=2[C:3]=1[CH:45]=[CH2:46])=[CH2:27]

참가 물질

8

반응물 5

HCID 11776TriphenylphosphineHCID 66189TetravinylstannaneHCID 433294Lithium ChlorideHCID 5352426Tin atomHCID 219855071-(6-Bromo-7-trifluoromethylsulfonyl-2-benzothiazolyl)-3-ethylurea

생성물 1

HCID 219856411-(6,7-Di-vinyl-2-benzothiazolyl)-3-ethylurea수율 39.4%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 887Methanol용매

반응 조건

온도
100 °C

실험 절차

Similar to the synthesis of Example 203, a mixture of 1-(6-bromo-7-trifluoromethylsulfonyl-2-benzothiazolyl)-3-ethylurea (0.100 g, 0.22 mmol), lithium chloride (0.078 g, 1.84 mmol, 8.4 eq), triphenylphosphine (0.034 g, 0.13 mmol, 0.6 eq), Pd(PPh3)2Cl2 (0.018 g, 0.026 mmol, 0.12 eq), tetravinyltin (0.080 mL, 0.44 mmol, 2.0 eq), and a crystal of 2,6-di-tert-butyl-4-methylphenol was purged with nitrogen gas, and was heated at about 100° C. for about 18 hours. Additional tin reagent (0.080 mL, 0.44 mmol, 2.0 eq) was added to the mixture after the first 2 hours. The mixture was taken up in MeOH, filtered, and concentrated. Purification by HPLC and flash chromatography on SiO2 with ethyl acetate/methylene chloride (1/4) gave the desired compound 0.014 g (23%). LC/MS 274.3 (M+1); LC retention time 2.32 min.

후처리

  1. customSimilar to the synthesis of Example 203
  2. customa crystal of 2,6-di-tert-butyl-4-methylphenol was purged with nitrogen gas
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by HPLC and flash chromatography on SiO2 with ethyl acetate/methylene chloride (1/4)

출처 및 근거

ORD 기록
ord-43344259a13143f2b751032583d652d5
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091227B2

연결된 노트

불러오는 중…