Sodium Bicarbonate → HCID 59128694, compound

HRID 1991133Notes

Reaction equation

HRID 1991133 reaction equation
Br[CH2:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([Br:14])[CH:12]=2)[NH:7][CH:6]=1)=O.[C:15]([N:22]1[CH2:27][CH2:26][CH:25]([C:28]([NH2:30])=[S:29])[CH2:24][CH2:23]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C([O-])(O)=O.[Na+]>C1COCC1>[C:18]([O:17][C:15]([N:22]1[CH2:27][CH2:26][CH:25]([C:28]2[S:29][CH:2]=[C:3]([C:5]3[C:13]4[C:8](=[N:9][CH:10]=[C:11]([Br:14])[CH:12]=4)[NH:7][CH:6]=3)[N:30]=2)[CH2:24][CH2:23]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2735648tert-Butyl 4-carbamothioylpiperidine-1-carboxylateHCID 597000532-Bromo-1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)ethan-1-one

Product 1

HCID 59128694HCID 59128694, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 70 (1.71 g, 5.38 mmol) in THF (20 mL) was added 1-Boc-4-aminothiocarbonyl piperidine (1.31 g, 5.36 mmol) and the solution was allowed to stir at r.t. for 3 h. The reaction mixture was then poured onto saturated aqueous NaHCO3 (50 mL) and extracted with AcOEt (2×50 mL). The combined organic portions were then evaporated to afford 71 (2.58 g, 5.41 mmol, 100%) as a white powder. 1H NMR (400 MHz, CDCl3) δ 1.43 (s, 9H), 1.64-1.84 (m, 4H), 2.07-2.17 (m, 2H), 2.81-2.94 (m, 2H), 3.13-3.24 (m, 1H), 7.17 (s, 1H), 7.74 (d, J=2.4 Hz, 1H), 8.32 (d, J=2.1 Hz, 1H), 8.48 (d, J=2.1 Hz, 1H), 8.97 (br s, 1H).

Workup

  1. extractionextracted with AcOEt (2×50 mL)
  2. customThe combined organic portions were then evaporated

Sources & evidence

ORD record
ord-5816d51e820240cbb0d2de4b1a3124d9
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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