2-Pyridinecarboxaldehyde → HCID 70652323, compound

HRID 1467334Notes

Reaction equation

HRID 1467334 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([C:19]([NH:21][C@@H:22]5[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]5)=[O:20])[CH:17]=4)[NH:12][N:11]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.[N:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH:34]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:18]4[C:13](=[CH:14][CH:15]=[C:16]([C:19]([NH:21][C@@H:22]5[CH2:27][CH2:26][CH2:25][N:24]([CH2:34][C:29]6[CH:30]=[CH:31][CH:32]=[CH:33][N:28]=6)[CH2:23]5)=[O:20])[CH:17]=4)[NH:12][N:11]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 70652246HCID 70652246, compound

Product 1

HCID 70652323HCID 70652323, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

In a flask, dichloromethane (1 mL) and acetic acid (2 drops) was added to (R)-3-(2,3-dihydrobenzofuran-5-yl)-N-(piperidin-3-yl)-1H-indazole-5-carboxamide (12 mg) and picolinaldehyde (7 mg). The reaction was stirred for 15 minutes. Sodium triacetoxyborohydride (28 mg) was added in one portion. The reaction was stirred overnight. The reaction was concentrated in vacuo and purified using prep LC/MS.

Workup

  1. stirringThe reaction was stirred overnight
  2. concentrationThe reaction was concentrated in vacuo
  3. custompurified

Sources & evidence

ORD record
ord-51c0c1fd7d5242308e553c7b2439c043
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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