Boron tribromide → HCID 16741729, compound

HRID 222474Notes

Reaction equation

HRID 222474 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[C:11](=[O:34])[NH:12][C:13](=[O:33])[C:14]=2[C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:24]CC4C=CC=CC=4)[CH:22]=3)[N:17]([CH3:32])[CH:16]=2)=[CH:2]1.B(Br)(Br)Br>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[C:11](=[O:34])[NH:12][C:13](=[O:33])[C:14]=2[C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([OH:24])[CH:22]=3)[N:17]([CH3:32])[CH:16]=2)=[CH:2]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 16741637HCID 16741637, compound

Product 1

HCID 16741729HCID 16741729, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-benzofuran-3-yl-4-(5-benzyloxy-1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione (31) (22 mg, 0.044 mmol) in 2 ml of dry dichloromethane was added dropwise boron tribromide (44 mg, 0.178 mmol) at −10° C. After 45 min, the reaction was quenched with saturated NaHCO3, and diluted with ethyl acetate. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated. The residue was purified by preparative TLC (ethyl acetate:hexane; 2:3) to afford product (11 mg, 68%). 1H NMR (DMSO-d6, 400 MHz) 3.81 (s, 3H), 6.21 (d, J=2.1 Hz, 1H), 6.59 (dd, J=2.2, 8.5 Hz, 1H), 6.96 (m, 2H), 7.18 (m, 2H), 7.60 (d, J=8.5 Hz, 1H), 7.86 (s, 1H), 8.23 (s, 1H), 8.67 (s, 1H), 11.12 (s, 1H); 13C NMR (DMSO-d6, 100 MHz) 14.5, 103.6, 106.1, 111.2, 111.8, 111.9, 112.5, 121.1, 122.2, 123.0, 125.0, 126.1, 127.0, 131.6, 133.2, 134.9, 147.3, 152.1, 154.6, 172.4, 172.7. FAB-HRMS calcd for C21H14N2O4+Na+: 381.0846; found: 381.0844.

Workup

  1. customthe reaction was quenched with saturated NaHCO3
  2. additiondiluted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC (ethyl acetate:hexane; 2:3)

Sources & evidence

ORD record
ord-f9ed0f58b2304d39a7b91771dda301ab
Source dataset
uspto-grants-2012_06
Patent number
US08207216B2

Reaction notes

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