Methoxymethyl-triphenylphosphonium chloride → Methyl 6-amino-4-(4-fluorophenyl)-2-(1-methylethyl)-5-(2-methoxyethenyl)nicotinate

HRID 29086노트

반응식

HRID 29086 반응식
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[NH2:30][C:31]1[N:36]=[C:35]([CH:37]([CH3:39])[CH3:38])[C:34]([C:40]([O:42][CH3:43])=[O:41])=[C:33]([C:44]2[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=2)[C:32]=1[CH:51]=O>O1CCCC1.C(OCC)(=O)C>[NH2:30][C:31]1[C:32]([CH:51]=[CH:2][O:3][CH3:4])=[C:33]([C:44]2[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=2)[C:34]([C:40]([O:42][CH3:43])=[O:41])=[C:35]([CH:37]([CH3:39])[CH3:38])[N:36]=1

참가 물질

6

반응물 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 11438468HCID 11438468, 화합물HCID 23665647Potassium tert-butoxide

생성물 1

HCID 69311814Methyl 6-amino-4-(4-fluorophenyl)-2-(1-methylethyl)-5-(2-methoxyethenyl)nicotinate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of (methoxymethyl)triphenyl-phosphonium chloride (260 mg, 0.75 mmol) in tetrahydrofuran (0.3 mL) was added, dropwise, a solution of potassium tert-butoxide (0.75 mL, 1.0 M in tetrahydrofuran). After 15 min, a solution of methyl 6-amino-4-(4-fluorophenyl)-5-formyl-2-(1-methylethyl)-3-pyridinecarboxylate (95 mg, 0.3 mmol) in tetrahydrofuran (0.3 mL) was added to the above mixture. The resulting mixture was stirred at room temperature for 2.5 h, diluted with ethyl acetate (15 mL) and washed with brine, dried (Na2SO4) and evaporated. The residue was purified by a silica gel chromatography (45 g column), eluting with 15% to 20% of ethyl acetate in hexanes to provide methyl 6-amino-4-(4-fluorophenyl)-2-(1-methylethyl)-5-(2-methoxyethenyl)nicotinate as a E/Z mixture (80 mg, 77%): LCMS (ESI, pos. ion spectrum) m/z 345 (M+H); HPLC (method 3) tR=2.4 min.

후처리

  1. additionwas added
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by a silica gel chromatography (45 g column)
  6. washeluting with 15% to 20% of ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-0fb5ef589eb044808bef91c1f48217a1
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420059B2

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