3-Pyridinecarboxaldehyde → HCID 58828515, compound

HRID 2358308Notes

Reaction equation

HRID 2358308 reaction equation
[NH2:1][CH:2]([CH2:25][O:26][Si:27]([C:40]([CH3:43])([CH3:42])[CH3:41])([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:3][N:4]1[C:13]([C:14]#[N:15])=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:22][CH3:23])[CH:10]=2)[C:5]1=[O:24].[N:44]1[CH:49]=[CH:48][CH:47]=[C:46]([CH:50]=O)[CH:45]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.C([O-])(O)=O.[Na+].CCOC(C)=O>[Si:27]([O:26][CH2:25][CH:2]([NH:1][CH2:50][C:46]1[CH:45]=[N:44][CH:49]=[CH:48][CH:47]=1)[CH2:3][N:4]1[C:13]([C:14]#[N:15])=[C:12]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:22][CH3:23])[CH:10]=2)[C:5]1=[O:24])([C:40]([CH3:43])([CH3:42])[CH3:41])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride2×HCID 59389238HCID 59389238, compound

Product 1

HCID 58828515HCID 58828515, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 86584982Sodium bicarbonate ethyl acetateSolvent

Procedure

To a solution of amine 94 (51 mg, 0.075 mmol) in dichloroethane (2 mL) was added pyridine 3-carboxaldehyde (0.017 mL, 180 mmol). After stirring at RT for 15 min NaBH(OAc)3 (48 mg, 0.23 mmol) was added. After stirring overnight, added 1.2 equiv aldehyde and 1.5 equiv NaBH(OAc)3. After stirring for 5 h, the reaction mixture was diluted with NaHCO3/EtOAc and stirred for 10 min. It was then partitioned between EtOAc and NaHCO3. The organic phase was washed once with brine then dried (Na2SO4) and concentrated. The product was purified by automated flash chromatography (70-100% EtOAc/hexane).

Workup

  1. additionwas added
  2. stirringAfter stirring for 5 h
  3. stirringstirred for 10 min
  4. customIt was then partitioned between EtOAc and NaHCO3
  5. washThe organic phase was washed once with brine
  6. dry with materialthen dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe product was purified by automated flash chromatography (70-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-5ce5447fe00f434ebd70bb81716fe8d1
Source dataset
uspto-grants-2010_07
Patent number
US07763614B2

Reaction notes

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