Hydrochloric Acid → HCID 68507519、化合物

HRID 1715391

反応式

HRID 1715391 の反応式
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]

参加物

7

反応物 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

生成物 1

HCID 68507519HCID 68507519、化合物収率 68%

試薬・触媒・溶媒 2

HCID 10311-Propanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1a85f1401cbe4be7a7302f4adddee2b9
出典データセット
uspto-grants-2010_09
特許番号
US07799805B2

関連ノート

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