Trifluoroacetic acid → 7-(5-methoxy-1H-indol-3-yl)-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine

HRID 1628065Notes

Reaction equation

HRID 1628065 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8](C(OC(C)(C)C)=O)[CH:7]=[C:6]2[C:19]1[N:31]([S:32]([C:35]2[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[C:22]2=[N:23][CH:24]=[C:25]3[CH:29]=[N:28][N:27]([CH3:30])[C:26]3=[C:21]2[CH:20]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:19]1[N:31]([S:32]([C:35]2[CH:41]=[CH:40][C:38]([CH3:39])=[CH:37][CH:36]=2)(=[O:34])=[O:33])[C:22]2=[N:23][CH:24]=[C:25]3[CH:29]=[N:28][N:27]([CH3:30])[C:26]3=[C:21]2[CH:20]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58382058tert-butyl 5-methoxy-3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-1-carboxylate

Product 1

HCID 583821087-(5-methoxy-1H-indol-3-yl)-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridineYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 5-methoxy-3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-1-carboxylate (1.75 g, 3.06 mmol; Preparation #D.1) in DCM (30 mL) was treated with TFA (5.9 mL, 77 mmol) and then stirred at rt. After about 3 h the mixture was concentrated and diluted with water (50 mL). The mixture was extracted with DCM (3×25 mL) then the combined organics were dried over anhydrous MgSO4, filtered then concentrated under reduced pressure. The material was purified by flash chromatography on 80 g of silica gel using 8:2 DCM/EtOAc as an eluent to give 7-(5-methoxy-1H-indol-3-yl)-1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (1.11 g, 77%): LC/MS (Table 2, Method a) Rt=2.34 min; MS m/z 472 (M+H)+.

Workup

  1. concentrationAfter about 3 h the mixture was concentrated
  2. additiondiluted with water (50 mL)
  3. extractionThe mixture was extracted with DCM (3×25 mL)
  4. dry with materialthe combined organics were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationthen concentrated under reduced pressure
  7. customThe material was purified by flash chromatography on 80 g of silica gel using 8:2 DCM/EtOAc as an eluent

Sources & evidence

ORD record
ord-b9049cf81d044a87a1ac2f3e2dbbb2ff
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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