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Carbon tetrabromide → Methyl 1-({6-ethyl-5-[5-(4-isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}methyl)azetidine-3-carboxylate

HRID 2247777
ノート
印刷プレビュー

反応式

HRID 2247777 の反応式
[CH2:1]([C:3]1[N:8]=[C:7]([CH2:9]O)[CH:6]=[CH:5][C:4]=1[C:11]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([CH3:25])[CH3:24])=[C:18]([CH3:26])[CH:17]=2)[O:13][N:12]=1)[CH3:2].C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.[NH:52]1[CH2:55][CH:54]([C:56]([O:58][CH3:59])=[O:57])[CH2:53]1.C(N(CC)C(C)C)(C)C>>[CH2:1]([C:3]1[N:8]=[C:7]([CH2:9][N:52]2[CH2:55][CH:54]([C:56]([O:58][CH3:59])=[O:57])[CH2:53]2)[CH:6]=[CH:5][C:4]=1[C:11]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([CH3:25])[CH3:24])=[C:18]([CH3:26])[CH:17]=2)[O:13][N:12]=1)[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 68522833(6-Ethyl-5-(5-(4-isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl)pyridin-2-yl)methanol

生成物 1

HCID 68521940
Methyl 1-({6-ethyl-5-[5-(4-isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}methyl)azetidine-3-carboxylate

実験手順

The crude product of the title compound was synthesized by conducting the similar reaction to that mentioned in Example 23 (23g) using {6-ethyl-5-[5-(4-isobutyl-3-methylphenyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}methanol (0.15 g, 0.42 mmol) that was obtained in Example 29 (29a), carbon tetrabromide (0.28 g, 0.84 mmol), triphenylphosphine (0.22 g, 0.84 mmol), methyl 3-azetidinecarboxylate hydrochloride (96 mg, 0.63 mmol), and N,N-diisopropylethylamine (0.22 ml, 1.3 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:1 to 2:1) as the eluent to afford the title compound (0.13 g) in a yield of 71% as a colourless oily product.

後処理

  1. customthe similar reaction to

出典と根拠

ORDレコード
ord-10ecaf0a7d3946819fe0e13199d22bee
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07687491B2

反応ノート

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