Ammonium Chloride → HCID 25004497、化合物

HRID 2196099ノート

反応式

HRID 2196099 の反応式
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3([O:16][C:7]=2[C:6]([C:17](OC)=[O:18])=[CH:5][CH:4]=1)[CH2:15][CH2:14][S:13][CH2:12][CH2:11]3.[Cl:21][C:22]1[CH:23]=[N:24][CH:25]=[C:26]([Cl:29])[C:27]=1[CH3:28].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[NH4+].[Cl-]>O1CCCC1>[Cl:21][C:22]1[CH:23]=[N:24][CH:25]=[C:26]([Cl:29])[C:27]=1[CH2:28][C:17]([C:6]1[C:7]2[O:16][C:10]3([CH2:15][CH2:14][S:13][CH2:12][CH2:11]3)[O:9][C:8]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:18]

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 109538273,5-Dichloro-4-methylpyridineHCID 59286716HCID 59286716、化合物

生成物 1

HCID 25004497HCID 25004497、化合物収率 67%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of methyl 7-methoxy-2′,3′,5′,6′-tetrahydro-spiro[1,3-benzodioxole-2,4′-(4H)-thiopyran]-4-carboxylate (40 mg, 0.14 mmol) and 3,5-dichloro-4-picoline (33 mg, 0.20 mmol) in tetrahydrofuran (1.1 mL) was cooled to 0° C. A 1.0 M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (0.41 mL, 0.41 mmol) was added and the reaction mixture was allowed to reach room temperature overnight. Saturated aqueous NH4Cl (20 mL) was added. The aqueous phase was extracted with dichloromethane (3×15 mL). The combined organic phase was dried over MgSO4 and evaporated to dryness under reduced pressure. Standard HPLC purification afforded 2-(3,5-dichloropyridine-4-yl)-1-(7-methoxy-2′,3′,5′,6′-tetrahydro-spiro[1,3-benzodioxole-2,4′-(4H)-thiopyran]-4-yl)ethanone (38 mg, 67%). 13C NMR (DMSO) δ 189.1, 148.2, 147.7, 147.0, 141.3, 134.5, 132.8, 122.0, 119.1, 113.0, 107.9, 56.3, 43.6, 35.9, 25.5.

後処理

  1. extractionThe aqueous phase was extracted with dichloromethane (3×15 mL)
  2. dry with materialThe combined organic phase was dried over MgSO4
  3. customevaporated to dryness under reduced pressure
  4. customStandard HPLC purification

出典と根拠

ORDレコード
ord-3becadd69c0f4597bf33f8c21933ec8c
出典データセット
uspto-grants-2012_12
特許番号
US08338431B2

反応ノート

読み込み中…