Boron tribromide → HCID 136158615, compound

HRID 643772Notes

Reaction equation

HRID 643772 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([CH:14]=[C:15]3[CH2:20][CH2:19][CH2:18][N:17]=[C:16]3[C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)[Br:28]>ClCCl>[BrH:28].[BrH:28].[N:17]1[CH2:18][CH2:19][CH2:20][C:15](=[CH:14][C:12]2[S:13][C:9]([C:6]3[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=3)=[CH:10][CH:11]=2)[C:16]=1[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 53629478HCID 53629478, compound

Product 1

HCID 136158615HCID 136158615, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a −70° C. solution of 3-[5-(4-methoxyphenyl)thiophen-2-ylmethylene]-3,4,5,6-tetrahydro[2,3′]bipyridinyl (20 mg, 0.05 mmol) in anhydrous dichloromethane (5 mL) was added 1.0 M BBr3 in dichloromethane (0.5 mL). The reaction mixture was maintained under an atmosphere of N2 at rt. for 6 h and an additional 0.5 ml BBr3 solution was added. The reaction mixture was maintained over night and was quenched with anhydrous methanol (1 mL) at −40° C., and was concentrated to 1 ml. This procedure was repeated twice and the residue was dried under high vacuum. The solid obtained was washed with ethyl acetate and was isolated, thus providing 15 mg of an orange solid: 1H NMR (DMSO-d6) δ 8.89 (m, 2H), 8.08 (m, 1H), 7.70 (m, 6H), 6.85 (m, 2H), 3.76 (m, 2H), 2.97 (m, 2H), 2.13 (m, 2H); MS (EI) m/z 347 (M++1).

Workup

  1. temperatureThe reaction mixture was maintained over night
  2. customwas quenched with anhydrous methanol (1 mL) at −40° C.
  3. concentrationwas concentrated to 1 ml
  4. customthe residue was dried under high vacuum
  5. customThe solid obtained
  6. washwas washed with ethyl acetate
  7. customwas isolated

Sources & evidence

ORD record
ord-f3d1ee66c24c4cc38e8f2ff9a1c2e1d3
Source dataset
uspto-grants-2010_04
Patent number
US07700630B2

Reaction notes

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