Trifluoroacetic acid → 5-bromo-2-(2-(4-(isopropylsulfonyl)phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)isoindolin-1-one

HRID 627792Notes

Reaction equation

HRID 627792 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([C:12]1[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([S:27]([CH:30]([CH3:32])[CH3:31])(=[O:29])=[O:28])=[CH:23][CH:22]=4)[N:19]=3)[N:14](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:13]=1)[CH2:5]2.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([C:12]1[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:22]=[CH:23][C:24]([S:27]([CH:30]([CH3:32])[CH3:31])(=[O:28])=[O:29])=[CH:25][CH:26]=4)[N:19]=3)[NH:14][CH:13]=1)[CH2:5]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 711436245-Bromo-2-[2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl]isoindolin-1-one

Product 1

HCID 711548835-bromo-2-(2-(4-(isopropylsulfonyl)phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)isoindolin-1-oneYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-bromo-2-[2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl]isoindolin-1-one (50 mg, 0.06634 mmol) suspended in DCM (2 mL) under N2 and triethylsilane (53 μL, 0.3317 mmol) then TFA (300 μL, 3.894 mmol) added. RM stirred overnight then concentrated. Residue partitioned between DCM and saturated NaHCO3 solution. Organic phase washed with brine then dried and concentrated to a yellow solid. Dried at 60° C. in a vacuum oven to give title compound as a pale yellow solid (17 mg, 49%); 1H NMR (400 MHz, DMSO) δ1.22 (6H, d), 3.50 (1H, sep), 5.54 (2H, s), 7.77 (2H, s), 7.99 (2H, d), 8.08 (1H, s), 8.51-8.55 (3H, m), 9.11 (1H, s), 12.36 (1H, brs) ppm; MS (ES+) 512.0.

Workup

  1. concentrationthen concentrated
  2. customResidue partitioned between DCM and saturated NaHCO3 solution
  3. washOrganic phase washed with brine
  4. customthen dried
  5. concentrationconcentrated to a yellow solid
  6. customDried at 60° C. in a vacuum oven

Sources & evidence

ORD record
ord-43315e6d71534a1ba1570aa7d54935fb
Source dataset
uspto-grants-2016_04
Patent number
US09309250B2

Reaction notes

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