Sodium Carbonate → 4-Ethynyl-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridine

HRID 1408057ノート

反応式

HRID 1408057 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]#[C:9][Si](C)(C)C)[CH:5]=[CH:4][N:3]=1.[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:19][C:18]=1B1OC(C)(C)C(C)(C)O1)([O-:16])=[O:15].C([O-])([O-])=O.[Na+].[Na+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>CC([O-])=O.CC([O-])=O.[Pd+2].COCCOC>[C:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:22]2[CH:21]=[C:20]([N:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)[CH:19]=[CH:18][C:17]=2[N+:14]([O-:16])=[O:15])[CH:7]=1)#[CH:9]

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 219853912-Chloro-4-(2-(trimethylsilyl)ethynyl)pyridineHCID 665874871-[4-Nitro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-piperidine

生成物 1

HCID 867059454-Ethynyl-2-(2-nitro-5-(piperidin-1-yl)phenyl)pyridine

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
75 °C

実験手順

A degassed mixture of 2-chloro-4-((trimethylsilyl)ethynyl)pyridine 24a, boronic ester 1.1e, 4.9 mL of 2 M aqueous Na2CO3, and 12 mL of DME was treated with 45 mg of XPHOS and 11 mg of Pd(OAc)2. The mixture was stirred at 75° C. for 1.5 h. The solvent was evaporated at reduced pressure and the residue was dissolved in 100 mL of dichloromethane. The solution was washed with water and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel chromatography eluting with a 0-20% gradient of EtOAc in CH2Cl2 to give 275 mg of product. MS (ESI, m/z) 308.1 [M+H]+.

後処理

  1. customThe solvent was evaporated at reduced pressure
  2. dissolutionthe residue was dissolved in 100 mL of dichloromethane
  3. washThe solution was washed with water
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel chromatography
  7. washeluting with a 0-20% gradient of EtOAc in CH2Cl2

出典と根拠

ORDレコード
ord-e64637a5694146099452b3d69a8dddb6
出典データセット
uspto-grants-2014_12
特許番号
US08916569B2

反応ノート

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