Carbon tetrabromide → HCID 69475736, compound

HRID 339609Notes

Reaction equation

HRID 339609 reaction equation
[C:1]([O:9][C@H:10]1[C@H:14]([F:15])[C@H:13]([N:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:18][C:17]2=[O:31])[O:12][C@@H:11]1[CH2:32]O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:35].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[C:1]([O:9][C@H:10]1[C@H:14]([F:15])[C@H:13]([N:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:18][C:17]2=[O:31])[O:12][C@@H:11]1[CH2:32][Br:35])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 69475822HCID 69475822, compound

Product 1

HCID 69475736HCID 69475736, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 3 (0.12 g, 0.27 mmol) and CBr4 (0.11 g, 0.33 mmol) in 5.0 mL of anhydrous CH2Cl2 was added PPh3 (0.12 g, 0.41 mmol) at 0° C. under N2 atmosphere. The resulting solution was stirred for 48 h at room temperature. The solvent was removed under reduced pressure and the residue was purified on silica gel column chromatography (Hexane:EtOAc=1:2 to 1:4 v/v) to give compound 4 (0.08 g, 0.16 mmol) in 60% yield. 1H NMR (CDCl3, 400 MHz) δ 8.95 (br, 1H), 8.14 (d, J=7.6, 1H), 8.05 (d, J=7.2, 2H), 7.92 (d, J=7.2, 2H), 7.62 (m, 3H), 7.52 (d, J=7.6, 1H), 7.48 (m, 3H), 6.06 (dd, J=15.2, 1.2, 1H), 5.63 (dd, J=4.8, 1.2, 0.5H), 5.50 (dd, J=4.8, 1.2, 0.5H), 5.44 (m, 1H), 4.68 (m, 1H), 3.92 (dd, J=12.0, 4.0, 1H), 3.77 (dd, J=12.0, 4.8, 1H); MS calcd for C23H19BrFN3O5 m/z 516.1 (M+H)+, found 518.3.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified on silica gel column chromatography (Hexane:EtOAc=1:2 to 1:4 v/v)

Sources & evidence

ORD record
ord-5f99a74e24404c09aab3a3c479ffd00c
Source dataset
uspto-grants-2014_11
Patent number
US08895531B2

Reaction notes

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