Formaldehyde → HCID 71285431, compound

HRID 1481720Notes

Reaction equation

HRID 1481720 reaction equation
Cl.[CH2:2]([C:4]1[CH:5]=[C:6]([C:26]([OH:28])=[O:27])[C:7](=[O:25])[NH:8][C:9]=1[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[C:14]([C@H:20]1[CH2:24][CH2:23][CH2:22][NH:21]1)=[CH:13]2)[CH3:3].[C:29]([O-])(O)=O.[Na+].C=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.CC(O)=O>[CH2:2]([C:4]1[CH:5]=[C:6]([C:26]([OH:28])=[O:27])[C:7](=[O:25])[NH:8][C:9]=1[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH3:19])[C:14]([C@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[CH3:29])=[CH:13]2)[CH3:3]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 71285018HCID 71285018, compound

Product 1

HCID 71285431HCID 71285431, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a suspension of (R)-5-ethyl-6-(1-methyl-2-(pyrrolidin-2-yl)-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid hydrochloride (59.1 mg, 0.15 mmol) in dichloroethane (2.0 mL) was added aqueous NaHCO3 (0.20 mL). Reaction mixture was stirred at room temperature for 10 min before solution of HCHO (37% aqueous, 50 μL, 0.67 mmol) was added followed by AcOH (˜0.20 mL) to pH˜3-4. Upon addition of NaBH(OAc)3 (150 mg, 0.70 mmol) reaction was stirred at room temperature for 1 h. Complete consumption of starting material was observed. Mixture was quenched with addition of solution of NaHCO3 (aqueous saturated, 2 mL) and product was extracted with DCM (3×5 mL). Organic phase was dried over Na2SO4 and solvent was concentrated. Residue was triturated with Et2O and solid was collected by filtration to afford (R)-5-ethyl-6-(1-methyl-2-(1-methylpyrrolidin-2-yl)-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (40.0 mg, 72%) as yellow solid.

Workup

  1. customReaction mixture
  2. additionwas added
  3. customconsumption of starting material
  4. customMixture was quenched with addition of solution of NaHCO3 (aqueous saturated, 2 mL) and product
  5. extractionwas extracted with DCM (3×5 mL)
  6. dry with materialOrganic phase was dried over Na2SO4 and solvent
  7. concentrationwas concentrated
  8. customResidue was triturated with Et2O and solid
  9. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-7a255e04d9024992a619b2e4070481fb
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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