Dichloromethane → HCID 118036474、化合物

HRID 1778018ノート

反応式

HRID 1778018 の反応式
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]

参加物

8

反応物 4

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

生成物 1

HCID 118036474HCID 118036474、化合物

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-c9cc8e62fc5a4ba4af5dea2498362bf4
出典データセット
uspto-grants-2016_02
特許番号
US09266883B2

反応ノート

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