Formaldehyde → HCID 59513619, compound

HRID 1159833Notes

Reaction equation

HRID 1159833 reaction equation
[CH2:1]=O.[NH:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1.[F:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][N:15]2[S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:11][C:10]=1[OH:27]>CCO>[F:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][N:15]2[S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[C:11]([CH2:1][N:3]2[CH2:7][CH2:6][CH2:5][CH2:4]2)[C:10]=1[OH:27]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 67241531HCID 67241531, compound2×

Product 1

HCID 59513619HCID 59513619, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Paraformaldehyde (20.6 mg, 0.686 mmol) and pyrrolidine (0.057 ml, 0.686 mmol) in EtOH (1 ml) was heated until a clear solution was obtained. The solution was added to 6-fluoro-1-(phenylsulfonyl)-1H-indol-5-ol (100 mg, 0.343 mmol; Intermediate 95) in EtOH (1 ml) and the mixture was heated at 90 oC for 10 min. Solvent was evaporated. Yield: 137 mg and ca. 20% of material was purified on Gilson HPLC using 15-45% MeCN in 50 nM ammonium hydrogencarbonate buffer. Yield: 21 mg (82%); white solid. MS (ESI+) for C19H19FN2O3S m/z 375 (M+H)+.

Workup

  1. customwas obtained
  2. temperaturethe mixture was heated at 90 oC for 10 min
  3. customSolvent was evaporated
  4. customYield: 137 mg and ca. 20% of material was purified on Gilson HPLC

Sources & evidence

ORD record
ord-c3ac793cf09a41ec9ed6afbad21a6c9a
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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