Sodium Carbonate → 3-(5-aminobenzo[b]thiophen-2-yl)-5-(1-(3-((tert-butyldimethylsilyl)oxy)propyl)-1H-tetrazol-5-yl)pyridin-2-amine

HRID 2199621Notes

Reaction equation

HRID 2199621 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16]([C:17]2[CH:18]=[C:19](I)[C:20]([NH2:23])=[N:21][CH:22]=2)=[N:15][N:14]=[N:13]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:33]2[S:37][C:36]3[CH:38]=[CH:39][C:40]([NH2:42])=[CH:41][C:35]=3[CH:34]=2)O1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C([O-])(=O)C.C([O-])(=O)C.[Pd+2]>[NH2:42][C:40]1[CH:39]=[CH:38][C:36]2[S:37][C:33]([C:19]3[C:20]([NH2:23])=[N:21][CH:22]=[C:17]([C:16]4[N:12]([CH2:11][CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[N:13]=[N:14][N:15]=4)[CH:18]=3)=[CH:34][C:35]=2[CH:41]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 1254677282-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-5-amineHCID 1317356955-(1-(3-((tert-butyldimethylsilyl)oxy)propyl)-1H-tetrazol-5-yl)-3-iodopyridin-2-amine

Product 1

HCID 1317356943-(5-aminobenzo[b]thiophen-2-yl)-5-(1-(3-((tert-butyldimethylsilyl)oxy)propyl)-1H-tetrazol-5-yl)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

To the solution of 5-(1-(3-((tert-butyldimethylsilyl)oxy)propyl)-1H-tetrazol-5-yl)-3-iodopyridin-2-amine (184 mg, 0.4 mmol, 1 eq), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophen-5-amine (165 mg, 1.5 eq), and triphenylphosphine (21 mg, 0.2 eq) in dioxane (2 mL) and aqueous sodium carbonate (2M, 0.8 mL, 4 eq) under nitrogen atmosphere, was added palladium diacetate (9 mg, 0.1 eq) and the reaction mixture was vigorously stirred at 40° C. for two hours. It was then partitioned between ethyl acetate and aqueous ammonium chloride. The organic layer was isolated, further washed with saturated aqueous sodium bicarbonate, brine, and dried with anhydrous sodium sulfate. The upper clear solution was decanted and concentrated down with silica gel. The mixture was subject to a gradient column chromatography (EtOAc-Hex 1:2 to 5:1) to yield 3-(5-aminobenzo[b]thiophen-2-yl)-5-(1-(3-((tert-butyldimethylsilyl)oxy)propyl)-1H-tetrazol-5-yl)pyridin-2-amine as an oil, which solidified in vacuo, in the amount of 127 mg.

Workup

  1. customIt was then partitioned between ethyl acetate and aqueous ammonium chloride
  2. customThe organic layer was isolated
  3. washfurther washed with saturated aqueous sodium bicarbonate, brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe upper clear solution was decanted
  6. concentrationconcentrated down with silica gel

Sources & evidence

ORD record
ord-c56bdcf23209431dbccc122e0df90634
Source dataset
uspto-grants-2016_06
Patent number
US09359336B2

Reaction notes

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