Sodium Bicarbonate → N-(7-Bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethyl-N-tetrahydro-2H-4-pyranylmethylamine

HRID 2253365Notes

Reaction equation

HRID 2253365 reaction equation
[Br:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:16][CH3:17])[C:10]([NH:11][CH2:12][CH:13]3[CH2:15][CH2:14]3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[O:18]1[CH2:23][CH2:22][CH:21]([CH:24]=O)[CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1>[Br:1][C:2]1[N:7]2[N:8]=[C:9]([CH2:16][CH3:17])[C:10]([N:11]([CH2:12][CH:13]3[CH2:14][CH2:15]3)[CH2:24][CH:21]3[CH2:22][CH2:23][O:18][CH2:19][CH2:20]3)=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 58801654N-(7-Bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethylamine

Product 1

HCID 58801666N-(7-Bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethyl-N-tetrahydro-2H-4-pyranylmethylamineYield 84.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(7-bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethylamine (106 mg) in tetrahydrofuran (3 mL) was added tetrahydropyran-4-carbaldehyde (123 mg) at room temperature, and then sodium triacetoxyborohydride (229 mg) was gradually added. After stirring the reaction mixture for 1 hour, saturated aqueous sodium bicarbonate was added thereto. The obtained mixture was extracted with ethyl acetate, and organic extract was washed with brine and then dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (10 g) and the title compound (120 mg) was obtained as a yellow oil from the ethyl acetate:n-hexane (1:6) fraction.

Workup

  1. extractionThe obtained mixture was extracted with ethyl acetate
  2. extractionorganic extract
  3. washwas washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (10 g)

Sources & evidence

ORD record
ord-a0f697c8a6064d308a01d3c331612914
Source dataset
uspto-grants-2008_01
Patent number
US07323569B2

Reaction notes

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