Formaldehyde → HCID 71089596, compound

HRID 331031Notes

Reaction equation

HRID 331031 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[C:4]([F:11])[CH:3]=1.[C:12]([BH3-])#N.[Na+].C=O>C(O)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH3:12])=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 247281696-Bromo-4-fluoro-1H-indole

Product 1

HCID 71089596HCID 71089596, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 6-bromo-4-fluoro-1H-indole (412 mg, 1.925 mmol) in acetic acid (10.600 mL) at RT was added sodium cyanoborohydride (605 mg, 9.62 mmol). Reaction mixture was stirred for 15 mins Paraformaldehyde (578 mg, 19.25 mmol) was then added and the reaction mixture was stirred at RT for 4 hours. Reaction mixture was quenched with saturated Na2CO3 aqueous solution (ca. 30 mL) and extracted with DCM (ca. 25 mL twice). The combined organic layers were dried over phase separator and solvent removed in vacuo. The resulting material was purified using chromatography on silica (eluted with 5-10% ethyl acetate/cyclohexane) to afford the title compound (180 mg). LCMS (A): m/z (M+H)+ 230/232, C9H9BrFN requires 229/231 (acidic).

Workup

  1. customReaction mixture
  2. additionwas then added
  3. customReaction mixture
  4. customwas quenched with saturated Na2CO3 aqueous solution (ca. 30 mL)
  5. extractionextracted with DCM (ca. 25 mL twice)
  6. customThe combined organic layers were dried over phase separator and solvent
  7. customremoved in vacuo
  8. customThe resulting material was purified

Sources & evidence

ORD record
ord-d66126a92fec4e7aad5fd15604d8df7c
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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