Boron tribromide → 5-Hydroxy-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one

HRID 2213676Notes

Reaction equation

HRID 2213676 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=[C:13]([C:15]1[NH:16][CH:17]=[CH:18][CH:19]=1)[CH3:14].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=[C:13]([C:15]1[NH:16][CH:17]=[CH:18][CH:19]=1)[CH3:14]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 695454525-Methoxy-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one

Product 1

HCID 695451805-Hydroxy-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-methoxy-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one; (0.12 g, 0.5 mmol) in dichloromethane (5 mL) was treated with BBr3 solution (1.5 mL of a 1M solution in dichloromethane, 1.5 mmol, 3.0 eq.). After stirring overnight at ambient temperature, the reaction was quenched by water (10 mL). The organic layer was separated. The aqueous layer was neutralized with saturated NaHCO3 solution and extracted with ethyl acetate (2×20 mL). The combined organic layers were concentrated. Reverse phase HPLC using acetonitrile/water afforded 5-hydroxy-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one; (0.04 g); 1H NMR (400 MHz, DMSO-d6) δ 2.74 (s, 3H), 6.38 (m, 1H), 6.62 (m, 1H), 6.70 (m, 1H), 7.08 (m, 1H), 7.20 (m, 1H), 7.32 (m, 1H), 8.96 (s, 1H), 10.78 (s, 1H) ppm.

Workup

  1. customthe reaction was quenched by water (10 mL)
  2. customThe organic layer was separated
  3. extractionextracted with ethyl acetate (2×20 mL)
  4. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-d5951c9fe0e442d39470d2214a88bef1
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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