4-Cyano-3-fluorobenzyl bromide → Methyl 1-(4-cyano-3-fluorobenzyl)imidazol-5-ylacetate

HRID 278174

반응식

HRID 278174 반응식
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:12]=[C:11]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[N:10]=[CH:9]2)C=CC=CC=1.[C:30]([C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Br)=[CH:34][C:33]=1[F:40])#[N:31]>C(#N)C>[C:30]([C:32]1[CH:39]=[CH:38][C:35]([CH2:36][N:10]2[C:11]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:12][N:8]=[CH:9]2)=[CH:34][C:33]=1[F:40])#[N:31]

참가 물질

4

반응물 2

HCID 27784664-Cyano-3-fluorobenzyl bromideHCID 105239671-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl ester

생성물 1

HCID 11108504Methyl 1-(4-cyano-3-fluorobenzyl)imidazol-5-ylacetate수율 164.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
50 °C

실험 절차

A solution of methyl 1-(triphenylmethyl)imidazol-4-ylacetate from Step B (0.536 g, 1.40 mmol) and 4-cyano-3-fluoro-benzylbromide from Example 1, Step D (0.300 g, 1.40 mmol) in dry acetonitrile (3 mL) was heated at 50° C. under argon for 2 hours, then the precipitate was collected by filtration. The filtrate was concentrated to a volume of 1 mL and then heated at 50° C. for a further 2 hours. The precipitate formed was collected and combined with the first crop to give a white solid (0.63 g). This solid was dissolved in MeOH (30 mL) and heated to reflux for 2 hours. The MeOH was removed under reduced pressure and the residue was partitioned between sat. aq. NaHCO3 (20 mL) and CHCl3 (30 mL). The aqueous layer was extracted further with CHCl3 (2×15 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography, eluting with 3% MeOH/0.3% NH4OH in CHCl3 to give the titled product as a white solid.

후처리

  1. filtrationthe precipitate was collected by filtration
  2. concentrationThe filtrate was concentrated to a volume of 1 mL
  3. customThe precipitate formed
  4. customwas collected

출처 및 근거

ORD 기록
ord-0122e786b6eb417a806b01b2d2cb78d8
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06358985B1

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