Sodium Bicarbonate → HCID 86668750, compound

HRID 473102Notes

Reaction equation

HRID 473102 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][CH:16]1[C:24]2[C:19](=[CH:20][C:21]([CH2:25][C:26]3[CH:27]=[C:28]([CH2:36][OH:37])[CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=3)=[CH:22][CH:23]=2)[CH2:18][CH2:17]1.[F:38][C:39]([F:49])([F:48])[C:40]1[C:41]([CH:46]=O)=[N:42][CH:43]=[CH:44][CH:45]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:35][C:32]([F:33])([F:34])[C:30]1[CH:29]=[C:28]([CH2:36][OH:37])[CH:27]=[C:26]([CH2:25][C:21]2[CH:20]=[C:19]3[C:24](=[CH:23][CH:22]=2)[CH:16]([NH:15][CH2:46][C:41]2[C:40]([C:39]([F:48])([F:38])[F:49])=[CH:45][CH:44]=[CH:43][N:42]=2)[CH2:17][CH2:18]3)[CH:31]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 147614703-(Trifluoromethyl)pyridine-2-carboxaldehydeHCID 66734486HCID 66734486, compound

Product 1

HCID 86668750HCID 86668750, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (40 mg, 0.19 mmol) was added to a solution of (3-((1-amino-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)phenyl)methanol (30 mg, 0.093) and 3-trifluoromethyl-2-formylpyridine (15 mg, 0.086 mmol) in DCM (1 mL). The reaction was stirred at rt for 24 h before aq. sat. NaHCO3 (2 mL) was added to the mixture was filtered over a phase separator. The organic filtrate was evaporated to dryness in a Genevac. The crude material was purified by prep. LCMS to afford the title compound (18.9 mg, 42.1%). MS (ESI): m/z [M+H]+ 481.2

Workup

  1. additionwas added to the mixture
  2. filtrationwas filtered over a phase separator
  3. customThe organic filtrate was evaporated to dryness in a Genevac
  4. customThe crude material was purified by prep

Sources & evidence

ORD record
ord-b451a2d7c0db428090359e385cdbb507
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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