Water → 3-bromo-7-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-thiazol]-2'-amine

HRID 335931Notes

Reaction equation

HRID 335931 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:15]3([CH2:19][S:18]C(N)=[N:16]3)[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([I:21])[CH:13]=3)[O:8][C:5]2=[N:6][CH:7]=1.[C:22](=[O:25])([O-])[O-].[K+].[K+].[CH3:28][Si:29]([CH2:32][CH2:33]OCCl)([CH3:31])[CH3:30].O.[CH3:38][N:39]([CH:41]=[O:42])[CH3:40]>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:15]3([CH2:19][S:18][C:38]([N:39]([CH2:40][O:25][CH2:22][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH2:41][O:42][CH2:33][CH2:32][Si:29]([CH3:31])([CH3:30])[CH3:28])=[N:16]3)[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([I:21])[CH:13]=3)[O:8][C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 584662053-bromo-7-iodo-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-thiazol]-2'-amine

Product 1

HCID 673835243-bromo-7-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-thiazol]-2'-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

3-Bromo-7-iodo-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-thiazol]-2′-amine (500 g, 1.055 mmol) and potassium carbonate (0.729 g, 5.27 mmol) were dissolved in DMF (7.03 mL) and stirred for 5 min. The reaction was cooled to 0° C. and SEM-Cl (0.561 mL, 3.16 mmol) was added slowly dropwise. The reaction was warmed to RT and stirred overnight. The mixture was poured into a separatory funnel containing water (25 mL) and EtOAc (15 mL). The aqueous layer was extracted with EtOAc (3×20 mL), and the combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (0-50% EtOAc:Hex) to afford 3-bromo-7-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-thiazol]-2′-amine, isolated as a pink solid.

Workup

  1. temperatureThe reaction was warmed to RT
  2. stirringstirred overnight
  3. additionThe mixture was poured into a separatory funnel
  4. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe material was purified via column chromatography (0-50% EtOAc:Hex)

Sources & evidence

ORD record
ord-afb57124c3454723bffaa3ae943da693
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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