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Dichloromethane → HCID 71090334, 화합물

HRID 710172
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HRID 710172 반응식
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[O:13][C:14]2[CH:20]=[CH:19][C:18](B3OC(C)(C)C(C)(C)O3)=[CH:17][C:15]=2[N:16]=1.FC(F)(F)S(O[C:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH:37]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>CN(C=O)C.O.CCOC(C)=O.O>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[C:12]1[O:13][C:14]2[CH:20]=[CH:19][C:18]([C:36]3[CH2:41][CH2:40][N:39]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:38][CH:37]=3)=[CH:17][C:15]=2[N:16]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 71257308HCID 71257308, 화합물

생성물 1

HCID 71090334HCID 71090334, 화합물수율 44.1%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 6228Dimethylformamide용매
HCID 22728543Water ethylacetate용매

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온도
80 °C

실험 절차

2-[2-fluoro-4-(methylsulfonyl)phenyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxa borolan-2-yl)benzo[d]oxazole (50 mg, 0.12 mmol), tert-butyl 4-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (39 mg, 0.12 mmol) and sodium carbonate (38 mg, 0.36 mmol) were dissolved in DMF (2 ml) under N2 atmosphere. This mixture was degassed with nitrogen for 30 mins and added Pd(dppf)2Cl2.CH2Cl2 (10 mg, 0.009 mmol). This mixture stirred at 80° C. for 90 mins in microwave. Reaction mixture diluted with water and work up (AcOEt/H2O) afforded the crude. Crude was purified by combiflash using a mixture of AcOEt and Petether (27:73) to afford the titled compound (25 mg) as an off-white solid. M.P.: 149-151° C. 1H-NMR (δ ppm, CDCl3, 400 MHz): 8.47 (t, J 7.4, 1H), 7.93-7.80 (m, 3H), 7.65-7.57 (m, 1H), 7.53-7.45 (m, 1H), 6.20-6.02 (m, 1H), 4.12 (bs, 2H), 3.68 (t, J 5.3, 2H), 3.13 (s, 3H), 2.65-2.55 (m, 2H), 1.50 (s, 9H).

후처리

  1. customThis mixture was degassed with nitrogen for 30 mins
  2. additionadded Pd(dppf)2Cl2
  3. customReaction mixture
  4. customafforded the crude
  5. customCrude was purified by combiflash
  6. additiona mixture of AcOEt and Petether (27:73)

출처 및 근거

ORD 기록
ord-179c40a2f50f4c53aed644f8a08a4c31
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09181214B2

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