Trimethyltin chloride → HCID 178454345, compound

HRID 389486Notes

Reaction equation

HRID 389486 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH:19]=[C:18]([C:20]3[CH:25]=[N:24][C:23]([N:26]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[C:22]4[O:41][CH:42]=[CH:43][C:21]=34)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].Cl[Sn:53]([CH3:56])([CH3:55])[CH3:54]>C1COCC1>[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH:19]=[C:18]([C:20]3[CH:25]=[N:24][C:23]([N:26]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])=[C:22]4[O:41][C:42]([Sn:53]([CH3:56])([CH3:55])[CH3:54])=[CH:43][C:21]=34)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14016Trimethyltin chlorideHCID 2724682Lithium diisopropylamideHCID 178454344HCID 178454344, compound

Product 1

HCID 178454345HCID 178454345, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (−78° C.) solution of di-tert-butyl {4-[1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]furo[2,3-c]pyridin-7-yl}imidodicarbonate (400 mg, 0.653 mmol) in anhydrous THF (10 mL) was added lithium diisopropylamide (2 M in THF, 1.6 mL, 3.3 mmol), and the mixture stirred for 30 minutes. Chlorotrimethylstannane (1 M in THF, 3.92 mL, 3.92 mmol) was added, and the mixture warmed to RT. The mixture was then cooled to −78° C., quenched by addition of glacial acetic acid (0.2 mL), and warmed to RT. The solution was adsorbed onto silica gel and purified by ISCO chromatography (10 to 20% EtOAc:heptane) to afford 347 mg (69%) of the title compound as a tan solid. 1H NMR (400 MHz, CDCl3): δ 0.10 (s, 6 H), 0.45 (s, 9 H), 0.92 (s, 9 H), 1.39 (s, 18 H), 1.50-1.62 (m, 2 H), 1.87-2.09 (m, 4 H), 2.24 (d, J=12.1 Hz, 2 H), 3.69-3.80 (m, 1 H), 4.21 (tt, J=11.5, 3.9 Hz, 1 H), 7.08-7.11 (m, 1 H), 7.78 (s, 1 H), 7.88-7.91 (m, 1 H), 8.31 (s, 1 H).

Workup

  1. temperatureThe mixture was then cooled to −78° C.
  2. customquenched by addition of glacial acetic acid (0.2 mL)
  3. temperaturewarmed to RT
  4. custompurified by ISCO chromatography (10 to 20% EtOAc:heptane)

Sources & evidence

ORD record
ord-b9f7fdacd7cb45f0ad870bde90588385
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

Loading…