Potassium Phosphate, Tribasic → HCID 86658496, compound

HRID 335957Notes

Reaction equation

HRID 335957 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:15]3([CH2:19][S:18][C:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[N:16]3)[C:14]3[CH:13]=[C:12]([Cl:28])[N:11]=[CH:10][C:9]=3[O:8][C:5]2=[CH:6][CH:7]=1.[F:29][C:30]1[C:35](B(O)O)=[CH:34][CH:33]=[CH:32][N:31]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[Cl:28][C:12]1[N:11]=[CH:10][C:9]2[O:8][C:5]3[C:4]([C:15]4([CH2:19][S:18][C:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[N:16]4)[C:14]=2[CH:13]=1)=[CH:3][C:2]([C:35]1[C:30]([F:29])=[N:31][CH:32]=[CH:33][CH:34]=1)=[CH:7][CH:6]=3

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27832702-Fluoropyridine-3-boronic acidHCID 86658497HCID 86658497, compound

Product 1

HCID 86658496HCID 86658496, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)Catalyst

Procedure

A vial was charged with tert-butyl 7-bromo-3-chloro-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-thiazole]-2′-ylcarbamate (0.250 g, 0.518 mmol), 2-fluoropyridin-3-ylboronic acid (0.15 g, 1.04 mmol), potassium phosphate (0.33 g, 1.55 mmol) and bis-(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.018 g, 0.026 mmol). The vial was sealed before evacuating and backfilling with nitrogen. The solids were suspended in 1,4-dioxane (2.22 mL) and water (0.37 mL). The vial was placed in a pre-heated 100° C. oil bath. The reaction was stirred for 1 h before cooling to RT. The reaction was diluted with water (30 mL) and extracted with ether (2×50 mL). The combined organic layers were washed sequentially with water and brine before drying over sodium sulfate. The solvent was removed under reduced pressure and the crude material was purified by silica gel chromatography to afford tert-butyl 3-chloro-7-(2-fluoropyridin-3-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-thiazole]-2′-ylcarbamate (0.21 g, 0.43 mmol, 83% yield).

Workup

  1. customThe vial was sealed
  2. custombefore evacuating
  3. customwas placed in a pre-heated 100° C.
  4. additionThe reaction was diluted with water (30 mL)
  5. extractionextracted with ether (2×50 mL)
  6. washThe combined organic layers were washed sequentially with water and brine
  7. dry with materialbefore drying over sodium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-da137530ebbd4970a2a586dbc33fff0d
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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