Boron tribromide → HCID 66583357, compound

HRID 2213674Notes

Reaction equation

HRID 2213674 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[CH:13][C:14]1[NH:15][CH:16]=[CH:17][CH:18]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]2=[CH:13][C:14]1[NH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69545137HCID 69545137, compound

Product 1

HCID 66583357HCID 66583357, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-methoxy-3-[(pyrrol-2-yl)methylene]indolin-2-one; (0.10 g, 0.4 mmol) in dichloromethane (5 mL) was treated with BBr3 solution (2.0 mL of a 1M solution in dichloromethane, 20 mmol, 5.0 eq.). After stirring overnight at ambient temperature, the reaction mixture was concentrated. The resulting oil was chromatographed on SiO2 (5 g) using 1:3 hexane/ethyl acetate to afford 5-hydroxy-3-[(pyrrol-2-yl)methylene]indolin-2-one; (0.04 g); 1H NMR (400 MHz, DMSO-d6) δ 6.30 (m, 1H), 6.60 (m, 2H), 6.78 (m, 1H), 6.98 (m, 1H), 7.32 (m, 1H), 7.58 (m, 1H), 9.00 (s, 1H), 10.60 (s, 1H) ppm.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe resulting oil was chromatographed on SiO2 (5 g)

Sources & evidence

ORD record
ord-bbd7669f72464759b437125b61afbf97
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

Loading…