Acetic Acid → HCID 136963105, compound

HRID 628395Notes

Reaction equation

HRID 628395 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[N:14][C:15]([N:19](C(OC(C)(C)C)=O)[NH:20][C:21](OC(C)(C)C)=O)=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:35]([F:38])([F:37])[F:36])(=O)=O)C=CC=CC=1.[C:39](O)(=O)C>>[CH3:39][C:21]1[N:14]2[C:13]3[CH:12]=[C:11]([C:35]([F:38])([F:37])[F:36])[NH:10][C:18]=3[CH:17]=[CH:16][C:15]2=[N:19][N:20]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 118159504HCID 118159504, compound

Product 1

HCID 136963105HCID 136963105, compound

Procedure

A solution of di-tert-butyl 1-[1-(phenylsulfonyl)-2-(trifluoro methyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]hydrazine-1,2-dicarboxylate (0.66 g, 1.2 mmol, from Step 3) in acetic acid (20 mL) was heated at 180° C. for 5 minutes in the microwave. The acetic acid was removed in vacuo. The residue was dissolved in EtOAc and washed with an additional NaHCO3 solution. The organic layer was dried over sodium sulfate, filtered and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-10% MeOH in DCM. Yield: (0.14 g, 49%).

Workup

  1. customThe acetic acid was removed in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with an additional NaHCO3 solution
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by flash chromatography
  8. washeluting with a gradient from 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-be619be6cf994226956bdc481541546c
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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