Potassium tert-butoxide → HCID 22676722, compound

HRID 1006251Notes

Reaction equation

HRID 1006251 reaction equation
[C:1]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].Cl[C:32]1[C:37]([C:38]([F:41])([F:40])[F:39])=[CH:36][CH:35]=[CH:34][C:33]=1[S:42](C1C=CC=C(C(F)(F)F)C=1Cl)(=[O:44])=[O:43]>O1CCCC1.C(OCC)(=O)C>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:42]([C:33]3[CH:34]=[CH:35][CH:36]=[C:37]([C:38]([F:39])([F:40])[F:41])[CH:32]=3)(=[O:44])=[O:43])[C:8]=2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 69919277HCID 69919277, compoundHCID 87957054HCID 87957054, compound

Product 1

HCID 22676722HCID 22676722, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of tert-butyl-3-(4-methoxyphenyl)indole-2-carboxylate (Example 105, 75 mg, 0.23 mmol) in tetrahydrofuran (0.4 mL) was added potassium tert-butoxide (1 M in tetrahydrofuran, 0.4 mL) in one aliquot. After 10 minutes chloro[3-(trifluoromethyl)phenyl]sulfone (113 mg, 0.46 mmol) was added. The reaction mixture was stirred at room temperature overnight. The resulting mixture was diluted with ethyl acetate (4 mL) and quenched with water (2 mL). The organic phase was extracted with ethyl acetate (3×4 mL). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was filtered through a plug of silica gel (30% ethyl acetate/hexane) to provide tert-butyl 3-(4-methoxyphenyl)-1-{[3-(trifluoromethyl)phenyl]sulfonyl}indole-2-carboxylate (45 mg, 37%), which was used in the next step without further purification.

Workup

  1. customquenched with water (2 mL)
  2. extractionThe organic phase was extracted with ethyl acetate (3×4 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe crude product was filtered through a plug of silica gel (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3ef5d3551d734bbea74c4fea7fcd8045
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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