Methyl iodide → (+/-)-tert-Butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

HRID 2174122ノート

反応式

HRID 2174122 の反応式
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH2:11][C:12]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH3:23])=[C:17]4[C:13]=3[CH:14]=[CH:15][N:16]4[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[N:8][C:7]=2[CH:31]=1)#[N:2].CI.[Li+].[CH3:35][Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([C:12]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([CH3:23])=[C:17]4[C:13]=3[CH:14]=[CH:15][N:16]4[C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH3:35])=[N:8][C:7]=2[CH:31]=1)#[N:2]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 86701743tert-Butyl 4-((5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

生成物 1

HCID 86701764(+/-)-tert-Butyl 4-(1-(5-cyanobenzo[d]oxazol-2-yl)ethyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of tert-butyl 4-((5-cyanobenzo[d]oxazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (Example 144-A) (277 mg, 0.664 mmol) in THF (3.3 mL) was added MeI (0.050 mL, 0.796 mmol) at −78° C. At this point, LHMDS (0.730 mL, 0.730 mmol) was added at the same temperature and the reaction was allowed to warm up to rt over one hour and stirred at rt for 16 hrs. The reaction mixture was quenched at −78° C. with a saturated ammonium chloride (aq.) solution, diluted with water and DCM, passed through a phase separator, concentrated and purified via FCC (12 g column): Heptane/AcOEt:100/0 to 50/50 to obtain the title compound. MS (ESI+) m/z 432.4 (M+H).

後処理

  1. customThe reaction mixture was quenched at −78° C. with a saturated ammonium chloride (aq.) solution
  2. additiondiluted with water and DCM
  3. concentrationconcentrated
  4. custompurified via FCC (12 g column)

出典と根拠

ORDレコード
ord-8af82672658a4377b84e79b27046476d
出典データセット
uspto-grants-2015_06
特許番号
US09056874B2

反応ノート

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