Boron Trichloride → HCID 59275511, compound

HRID 1025129Notes

Reaction equation

HRID 1025129 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[C:18]([O:24]C(C)C)=[CH:17][C:11]=3[C:12]=2[C:13]([NH:15][CH3:16])=[O:14])=[CH:4][CH:3]=1.ClB(Cl)Cl>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[C:18]([OH:24])=[CH:17][C:11]=3[C:12]=2[C:13]([NH:15][CH3:16])=[O:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 59275437HCID 59275437, compound

Product 1

HCID 59275511HCID 59275511, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(4-fluorophenyl)-5-isopropoxy-N-methyl-6-nitrobenzofuran-3-carboxamide (210.5 mg, 0.565 mmol) in CH2Cl2 (14 mL) at 0° C. under N2 was added trichloroborane (1.70 mL, 1.7 mmol) (1M solution in CH2Cl2). The mixture was then stirred at r.t. for 17 hr. The mixture was evaporated. The reddish orange residue was added 7 ml H2O, and then 3.5 ml 1N HCl, and left standing until the solid turned yellow. The yellow solid product was then filtered and washed with 3×3 ml H2O and dried (182 mg, 93%). 1H NMR (500 MHz, DMSO-d6) δ 10.18 (broad s, 1 H), 8.53 (m, 1 H), 8.31 (s, 1 H), 7.98 (apparent dd, J=8.85, 5.49, 2 H), 7.43 (apparent t, J=8.85, 2 H), 7.28 (s, 1 H,), 2.84 (appeared as d, J=4.58, 3 H). LC/MS were performed by using Shimadzu-VP instrument with UV detection at 220 nm and Waters Micromass. HPLC method: Solvent A=10% MeOH-90% H2O-0.1% TFA, Solvent B=90% MeOH-10% H2O-0.1% TFA, Start % B=0, Final % B=100, Gradient time=2 min, Stop time=3 min, Flow Rate=4 ml/min, Column: Xterra MS 7 um, C18, 3.0×50 mm; (ES+) m/z (M+H)+=331.21, HPLC Rt=1.442 min.

Workup

  1. customThe mixture was evaporated
  2. additionThe reddish orange residue was added 7 ml H2O
  3. wait3.5 ml 1N HCl, and left
  4. filtrationThe yellow solid product was then filtered
  5. washwashed with 3×3 ml H2O
  6. customdried (182 mg, 93%)
  7. customB=100, Gradient time=2 min
  8. customtime=3 min, Flow Rate=4 ml/min, Column

Sources & evidence

ORD record
ord-468def686cb44e1f9e6a2d3e59558a4d
Source dataset
uspto-grants-2014_05
Patent number
US08722688B2

Reaction notes

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