Dichloromethane → HCID 118036474, 화합물

HRID 1778018노트

반응식

HRID 1778018 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:6]=2[N:19]=1.[B-](F)(F)(F)[CH:21]=[CH2:22].[K+].C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:21]([C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:6]=2[N:19]=1)=[CH2:22]

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 10379064tert-Butyl 2-chloro-7,8-dihydro-5H-pyrido[2,3-b]azepine-9(6H)-carboxylateHCID 23679353Potassium vinyltrifluoroborate

생성물 1

HCID 118036474HCID 118036474, 화합물

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

A degassed mixture of tert-butyl 2-chloro-7,8-dihydro-5H-pyrido[2,3-b]azepine-9(6H)-carboxylate (690 mg, 2.44 mmol), potassium trifluoro(vinyl)borate (344 mg, 2.44 mmol), PdCl2(dppf). CH2Cl2 (199 mg, 0.244 mmol) and Cs2CO3 (2.00 g, 6.1 mmol) in THF (50 ml) and H2O (10 ml) was heated at 80° C. for 3.5 h. The reaction mixture was diluted with H2O and extracted with DCM (2×). The combined organic layers were dried over Na2SO4 and evaporated. The crude material was applied to a 120 g RediSep® silica column and purified by normal phase chromatography, eluting with 1:3 EtOAc/heptanes. Product-containing fractions were combined and evaporated to give the title compound as an off-white solid. (UPLC-MS 6) tR 1.18; ESI-MS 275.2 [M+H]+.

후처리

  1. extractionextracted with DCM (2×)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customevaporated
  4. custompurified by normal phase chromatography
  5. washeluting with 1:3 EtOAc/heptanes
  6. customevaporated

출처 및 근거

ORD 기록
ord-c9cc8e62fc5a4ba4af5dea2498362bf4
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266883B2

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