Water → 2-(5-allyloxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 549044Notes

Reaction equation

HRID 549044 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[C:4]([C:12]2[N:20]([S:21]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)(=[O:23])=[O:22])[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[CH:13]=2)=[CH:3]1.[CH3:31][C:32](C)([O-])[CH3:33].[K+].C(Br)C=C.O>CN(C)C=O>[CH2:33]([O:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([CH3:1])[CH:3]=[C:4]2[C:12]1[N:20]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[CH:13]=1)[CH:32]=[CH2:31]

Participants

6

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 224772511-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-5-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 224774022-(5-allyloxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridineYield 52.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-5-ol [2.1 g, Reference Example 14(a)] in dry dimethylformamide (50 mL) was treated with potassium tert-butoxide (620 mg) at 0° C. under nitrogen. After stirring for 10 minutes the mixture was treated with allyl bromide (480 μl) and then allowed to warm slowly to ambient temperature. Stirring was continued for a further 6 hours after which time the mixture was poured carefully into water and the aqueous phase extracted exhaustively with ethyl acetate. The combined organic extracts were washed twice with brine (100 mL), then dried over sodium sulfate and then evaporated. The residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:1, v/v) to give the title compound (1.2 g) as a yellow foam, m.p. 257-259° C. MS: 458 (MH+).

Workup

  1. stirringStirring
  2. waitwas continued for a further 6 hours
  3. extractionthe aqueous phase extracted exhaustively with ethyl acetate
  4. washThe combined organic extracts were washed twice with brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and pentane (1:1

Sources & evidence

ORD record
ord-b1107937eeb84a0aa28a0dc06030c2f3
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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