3-Fluoro-5-(tributylstannyl)pyridine → HCID 59834581, 화합물

HRID 271120

반응식

HRID 271120 반응식
[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[C:21](Br)[CH:20]=2)([C:9]2[CH:14]=[C:13]([CH2:15][CH3:16])[N:12]=[C:11]([CH2:17][CH3:18])[CH:10]=2)[N:3]=1.[F:27][C:28]1[CH:29]=[C:30]([Sn](CCCC)(CCCC)CCCC)[CH:31]=[N:32][CH:33]=1>CN(C=O)C.C1(P([Pd-](Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[N:6]([CH3:7])[C:5](=[O:8])[C:4]([C:9]2[CH:14]=[C:13]([CH2:15][CH3:16])[N:12]=[C:11]([CH2:17][CH3:18])[CH:10]=2)([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]([C:30]3[CH:31]=[N:32][CH:33]=[C:28]([F:27])[CH:29]=3)[CH:20]=2)[N:3]=1

참가 물질

5

반응물 2

HCID 468399773-Fluoro-5-(tributylstannyl)pyridineHCID 598345582-Amino-5-(3-bromo-4-fluorophenyl)-5-(2,6-diethyl-pyridin-4-yl)-3-methyl-3,5-dihydro-imidazol-4-one

생성물 1

HCID 59834581HCID 59834581, 화합물수율 68.2%

시약·촉매·용매 2

HCID 178479804HCID 178479804, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

A mixture of 2-amino-5-(3-bromo-4-fluorophenyl]-5-(2,6-diethyl-pyridin-4-yl)-3-methyl-3,5-dihydro-imidazol-4-one (0.12 g, 0.286 mmol), 5-fluoropyridin-3-yl(tributly)tin (0.166 g, 0.43 mmol) and bis(triphenylphosphino)palladium(II) chloride (0.016 g, 0.023 mmol) in DMF (5 mL) was degassed and heated at 150° C. for 0.5 h. The mixture was cooled to room temperature and diluted with ethyl acetate (50 mL) and 2% aqueous lithium chloride (20 mL). The organic layer was separated, washed with 2% aqueous lithium chloride, dried over sodium sulfate, filtered, and concentrated. Purification of the resultant residue by flash chromatography (silica, 97:3:0.25 methylene chloride/methanol/concentrated ammonium hydroxide) afforded the title product (0.085 g, 68%) as a white solid, mp 155-157° C.; 1H NMR (300 MHz, CD3OD) 8.55 (d, J=1.5 Hz, 1H), 8.49 (d, J=2.7 Hz, 1H), 7.82 (d, J=9.6 Hz, 1H), 7.60-7.57 (m, 2H), 7.27 (dd, J=10.2, 8.7 Hz, 1H), 7.15 (s, 2H), 3.13 (s, 3H), 2.74 (q, J=7.5 Hz, 4H), 1.23 (t, J=7.5 Hz, 6H); IR (ATR) 3064, 2969, 2935, 1733, 1670, 1597, 1459, 1412, 1328, 1228, 989, 881, 783, 702 cm−1; ESI MS m/z 436 [C24H23F2N5O+H]+. Anal. Calcd for C24H23F2N5O: C, 66.19; H, 5.32; N, 16.08.

후처리

  1. customwas degassed
  2. temperatureThe mixture was cooled to room temperature
  3. additiondiluted with ethyl acetate (50 mL) and 2% aqueous lithium chloride (20 mL)
  4. customThe organic layer was separated
  5. washwashed with 2% aqueous lithium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the resultant residue by flash chromatography (silica, 97:3:0.25 methylene chloride/methanol/concentrated ammonium hydroxide)

출처 및 근거

ORD 기록
ord-ad1f8cff7a69458ba30dd312e1f8adac
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452885B2

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