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

HRID 2114064
Notes
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Reaction equation

HRID 2114064 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:20]=[CH:21][C:22]5[O:26][CH2:25][CH2:24][C:23]=5[CH:27]=4)[CH:18]=[C:13]3[C:12]([C:28]3[CH:29]=[N:30][N:31](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:32]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([SiH](C(C)C)C(C)C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]4[CH:20]=[CH:21][C:22]5[O:26][CH2:25][CH2:24][C:23]=5[CH:27]=4)[CH:18]=[C:13]3[C:12]([C:28]3[CH:29]=[N:30][NH:31][CH:32]=3)=[CH:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 138754Silane, tris(1-methylethyl)-HCID 670513901-Benzenesulfonyl-5-(2,3-dihydro-benzofuran-5-yl)-3-(1-trityl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 670513891-Benzenesulfonyl-5-(2,3-dihydro-benzofuran-5-yl)-3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineYield 38%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 48 (187 mg, 0.270 mmol) in CH2Cl2 (2 mL) was added triisopropylsilane (0.14 mL), TFA (0.73 mL) and distilled water (6 drops). The mixture was stirred at room temperature for 1 h 30 min. The reaction was quenched and made neutral by addition of aqueous saturated NaHCO3 and diluted with EtOAc (200 mL) and water (100 mL). The aqueous layer was extracted further with CH2Cl2 (150 mL), the organic solutions were combined, dried (MgSO4) and concentrated to afford a light brown oily solid. Purification by preparative TLC (EtOAc) afforded 49 (45 mg, 38%) as an off white solid; 1H NMR (400 MHz, CDCl3+1 drop CD3OD) δ 2.62 (t, J=17.7, 8.6 Hz, 2H), 3.96 (t, J=17.3, 8.6 Hz, 2H), 6.22 (d, J=8.2 Hz, 1H), 6.65 (t, J=8.0, 2.4 Hz, 2H), 6.76 (s, 1H), 6.84-6.88 (m, 2H), 6.93-6.96 (m, 1H), 7.19 (s, 1H), 7.27 (s, 1H), 7.41 (s, 1H), 7.56 (d, J=7.9 Hz, 2H), 7.97 (s, 1H).

Workup

  1. distillationdistilled water (6 drops)
  2. customThe reaction was quenched
  3. additionmade neutral by addition of aqueous saturated NaHCO3
  4. additiondiluted with EtOAc (200 mL) and water (100 mL)
  5. extractionThe aqueous layer was extracted further with CH2Cl2 (150 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto afford a light brown oily solid
  9. customPurification by preparative TLC (EtOAc)

Sources & evidence

ORD record
ord-c423b69ce7ae40dbaa26e9eb76bdb237
Source dataset
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07432375B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes