Methanol → 7-Fluoro-3-(5-pyrrolidin-1-ylmethyl-thiophen-2-yl)-indole

HRID 644074Notes

Reaction equation

HRID 644074 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[F:19])[C:12]([C:20]3[S:21][C:22]([CH2:25][N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)=[CH:23][CH:24]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].CO>O>[F:19][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:18]=1[NH:10][CH:11]=[C:12]2[C:20]1[S:21][C:22]([CH2:25][N:26]2[CH2:27][CH2:28][CH2:29][CH2:30]2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 686951601-Benzenesulfonyl-7-fluoro-3-(5-pyrrolidin-1-ylmethyl-thiophen-2-yl)-indole

Product 1

HCID 686965927-Fluoro-3-(5-pyrrolidin-1-ylmethyl-thiophen-2-yl)-indoleYield 76.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-benzenesulfonyl-7-fluoro-3-(5-pyrrolidin-1-ylmethyl-thiophen-2-yl)-indole (0.20 g, 0.46 mmol) and potassium carbonate (0.25 g, 1.82 mmol) were treated with a mixture of methanol and water (3:1 v/v; 4 ml) and subjected to microwave irradiation at 100° C. for 600 s. The resulting suspension was then concentrated under reduced pressure and partitioned between dichloromethane (10 ml) and water (10 ml). The organic phase was separated and the aqueous phase washed with dichloromethane (10 ml). The combined organic layers were dried with sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography eluting with 0-10% (v/v) methanol in dichloromethane to afford 7-fluoro-3-(5-pyrrolidin-1-ylmethyl-thiophen-2-yl)-indole as a colourless solid (0.10 g, 0.35 mmol).

Workup

  1. customirradiation at 100° C. for 600 s
  2. concentrationThe resulting suspension was then concentrated under reduced pressure
  3. custompartitioned between dichloromethane (10 ml) and water (10 ml)
  4. customThe organic phase was separated
  5. washthe aqueous phase washed with dichloromethane (10 ml)
  6. dry with materialThe combined organic layers were dried with sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography
  9. washeluting with 0-10% (v/v) methanol in dichloromethane

Sources & evidence

ORD record
ord-4e14995c67164c5e81f55c6c91be149c
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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