Tributyltin Chloride → HCID 67117498, compound

HRID 1366144Notes

Reaction equation

HRID 1366144 reaction equation
[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]

Participants

6

Reactant 3

HCID 15096Tributyltin ChlorideHCID 86616747HCID 86616747, compoundHCID 178418918HCID 178418918, compound

Product 2

HCID 222AmmoniaHCID 67117498HCID 67117498, compoundYield 148%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-75add54ab8fa447ebd25ea3e162895a0
Source dataset
uspto-grants-2011_02
Patent number
US07893058B2

Reaction notes

Loading…