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

HRID 335932Notes

Reaction equation

HRID 335932 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:15]3([CH2:19][S:18][C:17]([N:20]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[N:16]3)[C:14]3[C:9](=[CH:10][CH:11]=[C:12](I)[CH:13]=3)[O:8][C:5]2=[N:6][CH:7]=1.[N:38]1[CH:43]=[CH:42][CH:41]=[C:40](B(O)O)[CH:39]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:15]3([CH2:19][S:18][C:17]([N:20]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[N:16]3)[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:40]4[CH:39]=[N:38][CH:43]=[CH:42][CH:41]=4)[CH:13]=3)[O:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 673835243-bromo-7-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)-5'H-spiro[chromeno[2,3-b]pyridine-5,4'-thiazol]-2'-amine

Product 1

HCID 673833213-bromo-7-(pyridin-3-yl)-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 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A vial was charged with 3-bromo-7-iodo-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-thiazol]-2′-amine (0.114 g, 0.155 mmol), pyridin-3-ylboronic acid (0.029 g, 0.233 mmol), potassium carbonate (0.107 g, 0.776 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.018 g, 0.016 mmol). The vial was flushed with Ar (g), then dioxane (1.035 mL) and water (0.517 mL) were added in sequence. The vial was sealed and heated at 80° C. for 2 hrs. After cooling to RT the reaction was diluted with EtOAc (25 mL) and washed with water (25 mL). The aqueous layer was extracted with EtOAc (3×15 mL), and the combined organic layers were washed with brine, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep 40 g, gradient elution 0-5% MeOH:DCM) to afford 3-bromo-7-(pyridin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-thiazol]-2′-amine as a white solid.

Workup

  1. customThe vial was flushed with Ar (g)
  2. additiondioxane (1.035 mL) and water (0.517 mL) were added in sequence
  3. customThe vial was sealed
  4. temperatureAfter cooling to RT the reaction
  5. additionwas diluted with EtOAc (25 mL)
  6. washwashed with water (25 mL)
  7. extractionThe aqueous layer was extracted with EtOAc (3×15 mL)
  8. washthe combined organic layers were washed with brine
  9. dry with materialdried with sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe material was purified via column chromatography (RediSep 40 g, gradient elution 0-5% MeOH:DCM)

Sources & evidence

ORD record
ord-c43d9a5d008a46fda1a5595367256c75
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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