Sodium Carbonate → HCID 76695337, 화합물

HRID 1868343노트

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HRID 1868343 반응식
Br[C:2]1[C:3]([CH:15]=[O:16])=[N:4][N:5]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=1.CC1(C)C(C)(C)OB([CH:25]=[CH:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:29]1[CH:30]=[CH:31][CH:32]=[C:27]([CH:26]=[CH:25][C:2]2[C:3]([CH:15]=[O:16])=[N:4][N:5]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=2)[CH:28]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 57982717HCID 57982717, 화합물HCID 667342383-[2-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-YL)-vinyl]-pyridine

생성물 1

HCID 76695337HCID 76695337, 화합물

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

After the solution of 4-bromo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole-3-carbaldehyde Compound 3a (570 mg, 1.87 mmol) and 3-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-vinyl]-pyridine Compound 3c (863 mg, 3.74 mmol) in dioxane (35 mL) was degassed by evacuating and purging with nitrogen. [1,1′-Bis(diphenylphosphino)-ferrocene]dichloropalladium(II) complex (Pd(dppf)2Cl2) (273 mg, 0.374 mmol) and sodium carbonate in water (3.74 mL, 2M) were added to the reaction mixture. The resultant suspension was purged again with nitrogen and heated at 120° C. for 30 min in a microwave reactor. After the solvent was removed in vacuo, the residue was dissolved in methanol and loaded to silica gel directly. The crude compound was eluted with a gradient of 4:1 to 2:1 hexane/ethyl acetate by flush chromatography to yield 4-(2-pyridin-3-yl-vinyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazole-3-carbaldehyde Compound 3d (385.6 mg, 0.624 mmol, 72% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ 10.26 (s, 1H), 8.75 (s, 1H), 8.55 (d, 1H), 7.91 (m, 3H), 7.54 (d, 1H), 7.50 (t, 2H), 7.34 (dd, 2H), 7.11 (d, 1H), 5.82 (s, 2H), 3.62 (t, 2H), 0.94 (t, 2H), 0 (s, 9H); MS (ESI) m/z: 330.1 (M+H+).

후처리

  1. customby evacuating
  2. custompurging with nitrogen
  3. customThe resultant suspension was purged again with nitrogen
  4. customAfter the solvent was removed in vacuo
  5. dissolutionthe residue was dissolved in methanol
  6. washThe crude compound was eluted with a gradient of 4:1 to 2:1 hexane/ethyl acetate
  7. customby flush chromatography

출처 및 근거

ORD 기록
ord-29ced1bcafd943899af28d4e043b491e
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07635703B2

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