Potassium Hydroxide → HCID 22663183, compound

HRID 380426Notes

Reaction equation

HRID 380426 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[CH:15]1([CH2:21]Br)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[OH-].[K+]>CC(C)=O.[I-].[Na+]>[CH:15]1([CH2:21][N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:6]=3)[C:2]([CH3:1])=[CH:3]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 137636Cyclohexane, (bromomethyl)-HCID 21938240Methyl 3-methyl-1H-indole-6-carboxylate

Product 1

HCID 22663183HCID 22663183, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of methyl 3-methyl-1 H-indole-6-carboxylate(10 g, Reference Example 30), cyclohexylmethylbromide (19 g), potassium hydroxide (12 g) and sodium iodide (0.1 g) in acetone (200 ml) was stirred at room temperature for 6 hours. The reaction mixture was evaporated. The residue was partitioned between ethyl acetate (250 ml) and water (250 ml). The aqueous layer was extracted three times with ethyl acetate (250 ml). The total combined organic phases were dried over sodium sulphate then evaporated. The residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (gradient elution, 0:10 to 1:9, v/v)to yield the title compound (9.5 g). NMR (CDCl3): δ0.90-1.10(m), 1.10-1.40(m), 1.60-1.90(m), 2.30(s), 3.90-4.00(m), 3.90(s), 7.00(s), 7.50-7.60(m), 7.70-7.80(m), 8.00(s). MH+271.

Workup

  1. customThe reaction mixture was evaporated
  2. customThe residue was partitioned between ethyl acetate (250 ml) and water (250 ml)
  3. extractionThe aqueous layer was extracted three times with ethyl acetate (250 ml)
  4. dry with materialwere dried over sodium sulphate
  5. customthen evaporated
  6. additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (
  7. washgradient elution, 0:10 to 1:9, v/v)to

Sources & evidence

ORD record
ord-7d9d4ebb1263494bbb467a40ad157ad8
Source dataset
uspto-grants-2001_10
Patent number
US06303600B1

Reaction notes

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