Triethylamine → 2-[1-(3-Iodo-benzoyl)-piperidin-4-ylmethoxy]-6-fluoro-benzonitrile

HRID 2177020

반응식

HRID 2177020 반응식
Cl.[F:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:4]=1[C:5]#[N:6].[I:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24].C(N(CC)CC)C>>[I:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23]([N:16]1[CH2:17][CH2:18][CH:13]([CH2:12][O:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:3]([F:2])[C:4]=2[C:5]#[N:6])[CH2:14][CH2:15]1)=[O:24]

참가 물질

4

반응물 3

HCID 8471TriethylamineHCID 743783-Iodobenzoyl chlorideHCID 66924378HCID 66924378, 화합물

생성물 1

HCID 669244412-[1-(3-Iodo-benzoyl)-piperidin-4-ylmethoxy]-6-fluoro-benzonitrile수율 95%

실험 절차

A mixture of 2-fluoro-6-(piperidin-4-ylmethoxy)-benzonitrile hydrochloride (200 mg; 0.7 mmol) (Example 123, Step 3) was stirred at room temperature with 3-iodobenzoyl chloride (187 mg; 0.7 mmol) and triethylamine (0.3 mL; 2.1 mmol) for 16 hours. Reaction was cooled and quenched with dilute HCl and mixture extracted with ethyl acetate (2×20 mL). Combined organics washed with water, saturated sodium bicarbonate, brine and dried over Na2SO4. Crude solid was obtained as 2-[1-(3-iodo-benzoyl)-piperidin-4-ylmethoxy]-6-fluoro-benzonitrile. (310 mg; 95% yield).

후처리

  1. customReaction
  2. temperaturewas cooled
  3. customquenched with dilute HCl and mixture
  4. extractionextracted with ethyl acetate (2×20 mL)
  5. washCombined organics washed with water, saturated sodium bicarbonate, brine
  6. dry with materialdried over Na2SO4

출처 및 근거

ORD 기록
ord-76863b292167455ca504e9565103942a
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09067897B2

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