Hydrochloric Acid → HCID 68507519, 화합물

HRID 1715391

반응식

HRID 1715391 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:14])=[C:6]([CH:13]=1)[C:7]([NH:9][CH:10]1[CH2:12][CH2:11]1)=[O:8].[CH3:15][O:16][CH2:17]/[CH:18]=[CH:19]/B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[Na+].[Na+].Cl>CN(C=O)C.C(O)CC>[Cl:14][C:5]1[CH:4]=[CH:3][C:2]([CH:19]=[CH:18][CH2:17][O:16][CH3:15])=[CH:13][C:6]=1[C:7]([NH:9][CH:10]1[CH2:12][CH2:11]1)=[O:8]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 48069835-bromo-2-chloro-N-cyclopropylbenzamideHCID 162174432-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 68507519HCID 68507519, 화합물수율 68%

시약·촉매·용매 2

HCID 10311-Propanol용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

5-Bromo-2-chloro-N-cyclopropyl-benzamide (19.3 g, 70.5 mmol) was dissolved in a mixture of DMF (350 mL) and 1-propanol (210 mL). Pd(OAc)2(PPh3)3 (2.64 g, 3.53 mmol) was added. (E)-2-(3-Methoxypropenyl)4,4,5,5-tetramethyl-1,3,2-dioxaborolane (15 mL, 70.5 mmol) was added through a syringe, and aq. 2M Na2CO3 (123 mL) was added. The mixture was stirred at 80° C. for 2 h, and allowed to cool to rt. Aq. 10% HCl was added carefully until a pH of 2 was reached. The solvents were partially removed under reduced pressure, and the residue was extracted with Et2O (3×). The combined org. extracts were washed with water and brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 1:2→1:1→EtOAc) yielded the title compound (12.7 g, 68%). LC-MS: tR=0.82 min; ES+: 266.17.

후처리

  1. temperatureto cool to rt
  2. customThe solvents were partially removed under reduced pressure
  3. extractionthe residue was extracted with Et2O (3×)
  4. washextracts were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customPurification of the residue by FC (EtOAc/heptane 1:2→1:1→EtOAc)

출처 및 근거

ORD 기록
ord-1a85f1401cbe4be7a7302f4adddee2b9
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799805B2

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