Tributyltin Chloride → HCID 67117498、化合物

HRID 1921768ノート

反応式

HRID 1921768 の反応式
[C:1]([O:5][C:6](=[O:31])[N:7]([C:21]1[C:22]2[N:23]([CH:28]=[CH:29][N:30]=2)[C:24](Br)=[CH:25][N:26]=1)[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C([Mg]Cl)(C)C.[CH2:37]([Sn:41](Cl)([CH2:46][CH2:47][CH2:48][CH3:49])[CH2:42][CH2:43][CH2:44][CH3:45])[CH2:38][CH2:39][CH3:40]>C1COCC1>[NH3:7].[C:1]([O:5][C:6](=[O:31])[N:7]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1)[C:21]1[C:22]2[N:23]([CH:28]=[CH:29][N:30]=2)[C:24]([Sn:41]([CH2:42][CH2:43][CH2:44][CH3:45])([CH2:46][CH2:47][CH2:48][CH3:49])[CH2:37][CH2:38][CH2:39][CH3:40])=[CH:25][N:26]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 15096Tributyltin ChlorideHCID 86616747HCID 86616747、化合物HCID 178418918HCID 178418918、化合物

生成物 2

HCID 222AmmoniaHCID 67117498HCID 67117498、化合物収率 148%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

In the same way as described for Compound 212, step 2, using a solution of (5-bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(4-methyl-piperazin-1-yl)-phenyl]-carbamic acid tert-butyl ester (0.3 g, 0.62 mmol) in THF (5 mL), and isopropylmagnesium chloride (0.46 mL of a 2M solution in THF, 0.67 mmol). After stirring for 5 min, tributyltin chloride (0.28 mL, 1.04 mmol) is added and the reaction is stirred at −78° C. for 10 min before being allowed to warm to room temperature. After stirring at room temperature for 30 min, the mixture is concentrated. The crude mixture is purified by silica gel flash column chromatography using 95:5 DCM:NH3 (7M in MeOH), to give [4-(4-methyl-piperazin-1-yl)-phenyl]-(5-tributylstannanyl-imidazo[1,2-a]pyrazin-8-yl)-carbamic acid tert-butyl ester (0.32 g, 70%) as a yellow oil. LCMS: Rt 7.03 min (92.3%), m/z (ES+) 695, 697, 699.

後処理

  1. stirringthe reaction is stirred at −78° C. for 10 min
  2. stirringAfter stirring at room temperature for 30 min
  3. concentrationthe mixture is concentrated
  4. customThe crude mixture is purified by silica gel flash column chromatography

出典と根拠

ORDレコード
ord-2b1e6fccebeb4fa58be113746f012119
出典データセット
uspto-grants-2012_05
特許番号
US08173656B2

反応ノート

読み込み中…