Sodium;azanide;benzyl(triphenyl)phosphanium;bromide → 2,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-(3-phenyl-2-propenyl)pyridine

HRID 324819노트

반응식

HRID 324819 반응식
C[O:2][C:3]([C:5]1[C:6]([CH:24]([CH3:26])[CH3:25])=[N:7][C:8]([CH:21]([CH3:23])[CH3:22])=[C:9]([CH2:18][CH:19]=O)[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=O.[Br-].[CH2:28]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[NH2-].[Na+]>C(OCC)(=O)C.CCCCCC>[CH:24]([C:6]1[C:5]([CH2:3][OH:2])=[C:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:9]([CH2:18][CH:19]=[CH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:8]([CH:21]([CH3:22])[CH3:23])[N:7]=1)([CH3:26])[CH3:25]

참가 물질

4

반응물 2

HCID 16211268Sodium;azanide;benzyl(triphenyl)phosphanium;bromideHCID 22005171Methyl-2,6-diisopropyl-4-(4-fluorophenyl)-5-(2-oxoethyl)-3-pyridinecarboxylate

생성물 1

HCID 545720632,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-(3-phenyl-2-propenyl)pyridine

시약·촉매·용매 1

HCID 21226206Ethyl acetate hexane용매

실험 절차

The title compound was prepared from the intermediate obtained in Step A and benzyl triphenylphosphonium bromide/sodium amide according to the procedures described in Example 1, Steps F-G. The product was obtained as a 6:4 mixture of trans:cis isomers. 1H NMR (300 MHz, CDCl3): δ 7.19 (m, 8 H), 6.96 (m, 1 H), 6.32 (d, J=11 Hz, 0.4 H), 6.09 (dt, J=5.5, 16 Hz, 0.6 H), 5.96 (d, J=16 Hz, 0.6 H), 5.45 (dt, J=7, 11 Hz, 0.4 H), 4.37 (d, J=5 Hz, 1.25 H), 4.33 (d, J=5.5 Hz, 0.75 H), 3.41 (m, 1.6 H), 3.25 (m, 2 H), 3.08 (m, 0.4 H), 1.35 (m, 5 H), 1.30 (d, J=6.6 Hz, 5 H), 1.21 (m, 3 H). FAB-MS: calcd for (C27H30FNO) 403, found 404 (M+H). Anal. Calcd for C27H30FNO: C, 80.36; H, 7.49; N, 3.47. Found: C, 80.15; H, 7.44; N, 3.26. mp 72-73° C. Rf=0.3 (20% ethyl acetate/hexane).

후처리

  1. customThe product was obtained as a 6:4 mixture of trans

출처 및 근거

ORD 기록
ord-a5f0d071af47416b9fae5a39be99c0f6
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06218431B1

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