Trifluoroacetic acid → HCID 135409736, compound

HRID 2078729Notes

Reaction equation

HRID 2078729 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[N:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:19]1[C:20]2[S:33][CH:32]=[CH:31][C:21]=2[N:22](C(OC(C)(C)C)=O)[N:23]=1)=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:18][O:17][C:13]1[N:12]=[C:11]2[CH:10]=[C:9]([C:19]3[C:20]4[S:33][CH:32]=[CH:31][C:21]=4[NH:22][N:23]=3)[NH:8][C:16]2=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 11430Potassium CarbonateHCID 57637301HCID 57637301, compound2×

Product 1

HCID 135409736HCID 135409736, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 2-(1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-methoxy-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester [250 mg, 0.531 mmol, Intermediate (62)], anisole (1.0 mL), and dichloromethane (1.0 mL) at ambient temperature was added trifluoroacetic acid (1.0 mL) and the resulting solution heated at 45° C. After 1 hour, the green reaction solution was cooled to ambient temperature, basified with 5% aqueous potassium carbonate (30 mL), and the resulting mixture extracted twice with ethyl acetate (20 mL). The combined extracts were washed with water (20 mL) and brine (20 mL) successively, dried over magnesium sulfate, and concentrated in vacuo to an oily mixture. Trituration with ether/heptane (1:1) provided 5-methoxy-2-(1H-thieno[3,2-c]pyrazol-3-yl)-1H-pyrrolo[3,2-b]pyridine [107 mg, 74%, Example 60] as a tan powder. TLC Rf 0.52 (silica, ethyl acetate); mp: 234-236° C.; LC/MS: 271.02 (M+H), RT=2.03 minutes; 1H NMR [300 Mhz, (CD3)2SO]: δ 13.32 (br s 1H), 11.67 (br s, 1H), 7.74 (d, J=5 Hz, 1H), 7.66 (d, J=9 Hz, 1H), 7.18 (d, J=5 Hz, 1H), 6.58-6.53 (m, 2H), 3.85 (s, 3H).

Workup

  1. temperaturethe green reaction solution was cooled to ambient temperature
  2. extractionthe resulting mixture extracted twice with ethyl acetate (20 mL)
  3. washThe combined extracts were washed with water (20 mL) and brine (20 mL) successively
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo to an oily mixture

Sources & evidence

ORD record
ord-0a24033d438a4568bb3c948940eda0f5
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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