Sodium Hydroxide → Methyl 2-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)acetate

HRID 913917ノート

反応式

HRID 913917 の反応式
[OH-].[Na+].[CH3:3]N(N=O)C(N[N+]([O-])=O)=N.[Cl:13][C:14]1[CH:22]=[C:21]([CH2:23][C:24]([OH:26])=[O:25])[C:20]2[C:16](=[CH:17][N:18]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[N:19]=2)[CH:15]=1>C(OCC)C>[Cl:13][C:14]1[CH:22]=[C:21]([CH2:23][C:24]([O:26][CH3:3])=[O:25])[C:20]2[C:16](=[CH:17][N:18]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:32])[CH3:34])[N:19]=2)[CH:15]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 575462532-(5-Chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)acetic acidHCID 135436526N-Methyl-N'-nitro-N-nitrosoguanidine

生成物 1

HCID 57545943Methyl 2-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)acetate

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

To a heterogeneous mixture of sodium hydroxide (4M in water, 25 mL) and diethyl ether (75 mL) at 0° C. was added N-methyl-N′-nitro-N-nitrosoguanidine (2.24 g, 15.3 mmol) with swirling (no stirbar). After addition was complete, the mixture was allowed to stand at 0° C. for 15 min with occasional swirling. The ethereal was transferred in portions to a suspension of 2-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)acetic acid (2.6 g, 7.63 mmol) in diethyl ether (50 mL) until the yellow color persisted and all of the starting material had gone into solution. The reaction was allowed to rest at room temperature for 5 min before bubbling nitrogen through the solution to remove most of the unreacted diazomethane. Column chromatography (25% ethyl acetate/n-hexane) gave 2.28 g (84%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ 8.02 (s, 1H), 7.56 (d, J=1.5 Hz, 1H), 7.14 (d, J=0.9 Hz, 1H), 5.67 (s, 2H), 4.01 (s, 2H), 3.70 (s, 3H), 3.61 (t, J=8.2 Hz, 2H), 0.92 (t, J=8.3 Hz, 2H), −0.04 (s, 9H); 13C NMR (126 MHz, CDCl3) δ ppm 171.3, 146.9, 127.7, 127.5, 126.0, 122.61, 122.57, 118.3, 82.0, 67.7, 52.1, 36.1, 17.9, −1.4.

後処理

  1. additionAfter addition
  2. waitto rest at room temperature for 5 min
  3. custombefore bubbling nitrogen through the solution
  4. customto remove most of the unreacted diazomethane
  5. customColumn chromatography (25% ethyl acetate/n-hexane) gave 2.28 g (84%) as a colorless oil

出典と根拠

ORDレコード
ord-753e34cde1564f6f842a60c512173bdf
出典データセット
uspto-grants-2011_09
特許番号
US08026257B2

反応ノート

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