Lithium Hexamethyldisilazide → 7-chloro-N-(1-((1-isopropyl-1H-pyrazol-3-yl)methyl)-3-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 706590ノート

反応式

HRID 706590 の反応式
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[NH2:11])[N:4]([CH2:12][C:13]2[CH:17]=[CH:16][N:15]([CH:18]([CH3:20])[CH3:19])[N:14]=2)[N:3]=1.[Cl:21][C:22]1[CH:27]=[CH:26][N:25]2[C:28]([C:31](OCC)=[O:32])=[CH:29][N:30]=[C:24]2[CH:23]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[Cl:21][C:22]1[CH:27]=[CH:26][N:25]2[C:28]([C:31]([NH:11][C:9]3[CH:8]=[CH:7][CH:6]=[C:5]4[C:10]=3[C:2]([CH3:1])=[N:3][N:4]4[CH2:12][C:13]3[CH:17]=[CH:16][N:15]([CH:18]([CH3:20])[CH3:19])[N:14]=3)=[O:32])=[CH:29][N:30]=[C:24]2[CH:23]=1

参加物

5

反応物 3

HCID 2733832Lithium HexamethyldisilazideHCID 67107280Ethyl 7-chloroimidazo[1,2-A]pyridine-3-carboxylateHCID 866993293-Methyl-1-((1-isopropylpyrazole-3-yl)methyl)-4-amino-1H-indazole

生成物 1

HCID 679740927-chloro-N-(1-((1-isopropyl-1H-pyrazol-3-yl)methyl)-3-methyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide収率 52%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

3-Methyl-1-((1-isopropylpyrazole-3-yl)methyl)-4-amino-1H-indazole (1 equivalent) and ethyl 7-chloroimidazo[1,2-a]pyridine-3-carboxylate (Example 7 step D; 1 equivalent) were dissolved in dry THF (0.2 M) and the resulting solution was cooled to 0° C. Lithium bis(trimethylsilyl)amide (2.3 equivalents) was slowly added and the resulting mixture was allowed to warm to ambient temperature overnight. THF was removed under vacuum and the remaining material was partitioned between water and ethyl acetate. The bottom aqueous layer was extracted twice with ethyl acetate. The combined organic extracts were combined, dried over sodium sulfate, filtered and \ concentrated to give desired compound (52% yield).

後処理

  1. temperatureto warm to ambient temperature overnight
  2. customTHF was removed under vacuum
  3. customthe remaining material was partitioned between water and ethyl acetate
  4. extractionThe bottom aqueous layer was extracted twice with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentration\ concentrated

出典と根拠

ORDレコード
ord-2f49b428d034488fab4c6531f458e028
出典データセット
uspto-grants-2015_11
特許番号
US09174981B2

反応ノート

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