Trifluoroacetic acid → 1-Benzenesulfonyl-5-morpholin-4-yl-3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 2114072Notes

Reaction equation

HRID 2114072 reaction equation
C([SiH](C(C)C)C(C)C)(C)C.FC(F)(F)C(O)=O.[C:18]1([S:24]([N:27]2[C:31]3=[N:32][CH:33]=[C:34]([N:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)[CH:35]=[C:30]3[C:29]([C:42]3[CH:43]=[N:44][N:45](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:46]=3)=[CH:28]2)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCCCCC.CCOC(C)=O.O>[C:18]1([S:24]([N:27]2[C:31]3=[N:32][CH:33]=[C:34]([N:36]4[CH2:37][CH2:38][O:39][CH2:40][CH2:41]4)[CH:35]=[C:30]3[C:29]([C:42]3[CH:46]=[N:45][NH:44][CH:43]=3)=[CH:28]2)(=[O:26])=[O:25])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 138754Silane, tris(1-methylethyl)-HCID 516892Sodium BicarbonateHCID 670513961-Benzenesulfonyl-5-morpholin-4-yl-3-(trityl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 689732081-Benzenesulfonyl-5-morpholin-4-yl-3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 64.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Triisopropylsilane (0.058 mL, 0.28 mmol), trifluoroacetic acid (TFA, 0.2 mL) and water (0.02 mL) were added to a solution of 56 (0.093 g, 0.14 mmol) in CH2Cl2 (2 mL). After string for 15 minutes, the pH of the mixture was adjusted to pH 7-8 with saturated aqueous NaHCO3 and product was extracted with CH2Cl2 twice. The combined organic solutions was dried (MgSO4) and concentrated to afford a tan syrup. Hexane:AcOEt (1:1) solution of was added to the syrup and the mixture was cooled with ice-water bath. The precipitate was filtered off, washed with hexane and dried to afford 57 (0.037 g, 63%) as a brown solid. 1H NMR (400 MHz, CDCl3) δ 3.06-3.10 (m, 4H), 3.80-3.84 (m, 4H), 7.34 (d, J=0.27 Hz, 1H), 7.39-7.44 (m, 2H), 7.48-7.53 (m, 1H), 7.68 (s, 1H), 7.79 (bs, 1H), 8.09-8.13 (m, 2H), 8.18 (d, J=0.27 Hz, 1H).

Workup

  1. extractionwas extracted with CH2Cl2 twice
  2. dry with materialThe combined organic solutions was dried (MgSO4)
  3. concentrationconcentrated
  4. customto afford a tan syrup
  5. temperaturethe mixture was cooled with ice-water bath
  6. filtrationThe precipitate was filtered off
  7. washwashed with hexane
  8. customdried

Sources & evidence

ORD record
ord-1f3dc5e786664e68b5b0da70828dfbe8
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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