Sodium Carbonate → 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-N-(2-methoxy-phenyl)-benzamide

HRID 661641ノート

反応式

HRID 661641 の反応式
C([O-])([O-])=O.[Na+].[Na+].[Cl:7][C:8]1[CH:24]=[CH:23][C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])=[O:13])=[CH:10][C:9]=1B1OC(C)(C)C(C)(C)O1.Br[C:35]1[C:40]([Cl:41])=[CH:39][C:38]([Cl:42])=[CH:37][N:36]=1>C1(C)C=CC=CC=1.CCO.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:7][C:8]1[CH:24]=[CH:23][C:11]([C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:21][CH3:22])=[O:13])=[CH:10][C:9]=1[C:35]1[C:40]([Cl:41])=[CH:39][C:38]([Cl:42])=[CH:37][N:36]=1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 8170902-Bromo-3,5-dichloropyridineHCID 686032344-chloro-N-(2-methoxy-phenyl)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide

生成物 1

HCID 686027194-chloro-3-(3,5-dichloro-pyridin-2-yl)-N-(2-methoxy-phenyl)-benzamide収率 67.1%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A solution of 2N Na2CO3 (5.85 mL) and Pd(PPh3)4 (340 mg, 0.29 mmol) was added to a degassed mixture of 4-chloro-N-(2-methoxy-phenyl)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (2.2 g, 5.85 mmol) and 2-bromo-3,5-dichloro-pyridine (1.47 g, 6.44 mmol) in toluene (30 mL) and EtOH (6 mL). The mixture was heated at 100° C. for 12 hrs. Upon cooling to room temperature, the mixture was diluted with ethyl acetate and washed with water and brine, and was dried over Na2SO4. After filtration and concentration the mixture was taken up in EtOAc, filtered, washed with EtOAc (3×), MeOH and ether to yield 1.6 g of 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-N-(2-methoxy-phenyl)-benzamide. MS [M+H]+: 406.9; tR=3.03 min. (method 1)

後処理

  1. temperatureUpon cooling to room temperature
  2. washwashed with water and brine
  3. dry with materialwas dried over Na2SO4
  4. filtrationAfter filtration and concentration the mixture
  5. filtrationfiltered
  6. washwashed with EtOAc (3×), MeOH and ether

出典と根拠

ORDレコード
ord-0cb5e9ded5874e11bd13ffb26668692a
出典データセット
uspto-grants-2011_12
特許番号
US08084614B2

反応ノート

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