tert-Butanol → 3,3-Dibromo-1H-pyrrolo[2,3-b]pyridin-2(3H)-one

Technical (90%) pyridinium tribromide (220.4 g, 0.62 mol) was added portionwise over a period of 30 min to a stirred suspension of 7-azaindole (1, 27.13 g, 0.23 mol) in t-BuOH (1.36 L). The mixture was stirred at r.t for 3 h, and more pyridinium tribromide (73.3 g, 0.21 mol) was added in one portion. After additional stirring at r.t. for 2 h, the solvent was evaporated under reduced pressure. The residue was separated between water:AcOEt=1:1 (4.2 L). The aqueous layer was extracted with AcOEt (2×800 mL). Combined organic solutions were washed with water (2×500 mL), brine, dried (MgSO4) and concentrated to dyness in vacuum. The residue was triturated with CH2Cl2 (1500 mL) for 20 min. The solid was filtered off, washed with CH2Cl2 (250 mL) and dried in vacuum to afford 2 (49.85 g, 75%) as yellow powder. 1H NMR (400 MHz, DMSO-d6) δ 7.16 (dd, J=7.4, 5.1 Hz, 1H), 7.98 (dd, J=7.4, 1.5 Hz, 1H), 8.19 (dd, J=5.1, 1.5 z, 1H), 11.97 (bs, 1H).

1. stirringAfter additional stirring at r.t. for 2 h
2. customthe solvent was evaporated under reduced pressure
3. customThe residue was separated between water
4. extractionThe aqueous layer was extracted with AcOEt (2×800 mL)
5. washCombined organic solutions were washed with water (2×500 mL), brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated to dyness in vacuum
8. customThe residue was triturated with CH2Cl2 (1500 mL) for 20 min
9. filtrationThe solid was filtered off
10. washwashed with CH2Cl2 (250 mL)
11. customdried in vacuum

ORDレコード

ord-738a47de4aa9466c9d4f31c302db40b0

出典データセット

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07534800B2