Sodium Carbonate → 2-Chloro-4-(5-formyl-pyridin-3-yl)-benzonitrile

HRID 391283

반응식

HRID 391283 반응식
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.CC1(C)C(C)(C)OB([C:19]2[CH:20]=[N:21][CH:22]=[C:23]([CH:26]=2)[CH:24]=[O:25])O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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:10][C:4]1[CH:3]=[C:2]([C:19]2[CH:20]=[N:21][CH:22]=[C:23]([CH:24]=[O:25])[CH:26]=2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 49926405-(Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbaldehydeHCID 70104204-Bromo-2-chlorobenzonitrile

생성물 1

HCID 595783972-Chloro-4-(5-formyl-pyridin-3-yl)-benzonitrile

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 4-bromo-2-chlorobenzonitrile (1.082 g, 5 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinaldehyde (1.165 g, 5.00 mmol), Pd(PPh3)4 (0.144 g, 0.125 mmol), sodium carbonate (2.5 mL, 5.00 mmol) in 1,4-dioxane (20 mL) was heated to reflux for 6 h. After cooling to room temperature, the solid was filtered and washed by ethyl acetate and water. After drying under vacumn, yellow powder was collected (1 g). 1H NMR (400 MHz, CDCl3): δ 7.63 (dd, J=1.68, 8 Hz, 1H), 7.79 (d, J=1.68 Hz, 1H), 7.83 (d, J=8 Hz, 1H), 8.35 (dd, J=2.24 Hz, 2.04 Hz, 1H), 9.07 (d, J=2.36 Hz, 1H), 9.15 (d, J=1.88 Hz, 1H), 10.22 (s, 1H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 6 h
  3. filtrationthe solid was filtered
  4. washwashed by ethyl acetate and water
  5. customAfter drying under vacumn, yellow powder
  6. customwas collected (1 g)

출처 및 근거

ORD 기록
ord-a87afc1f2deb48afa22eb7d07f862bdc
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383827B2

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