Carbon tetrabromide → HCID 86598339, compound

HRID 1270418Notes

Reaction equation

HRID 1270418 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([C:13]([N:15]2[C@H:20]([CH2:21][C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)[CH2:19][N:18]3[CH2:31][C@@H:32](O)[CH2:33][CH2:34][C@@H:17]3[CH2:16]2)=[O:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(Br)(Br)(Br)[Br:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([C:13]([N:15]2[C@H:20]([CH2:21][C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)[CH2:19][N:18]3[CH2:31][CH:32]([Br:39])[CH2:33][CH2:34][C@@H:17]3[CH2:16]2)=[O:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86598340HCID 86598340, compound

Product 1

HCID 86598339HCID 86598339, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 3,5-bis(trifluoromethyl)phenyl-[(3R,7S,9aR)-7-hydroxy-3-(1H-indol-3-ylmethyl)-octahydropyrido[1,2-a]pyrazin-2-yl]-methanone (3.85 g) in acetonitrile was added carbon tetrabromide (11.6 g) and triphenylphosphine (9.18 g), the resulting mixture was stirred at room temperature overnight. The formed precipitate was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by flash-chromatography (SiO2, CH2Cl2/MeOH 98:2) to afford 3,5-bis(trifluoromethyl)phenyl-[(3R,9aR)-7-bromo-3-(1H-indol-3-ylmethyl)-octahydropyrido[1,2-a]pyrazin-2-yl]-methanone (3.5 g). MH+ 588, Rf 0.38 (CH2Cl2/MeOH 97:3) (intermediate 17).

Workup

  1. customThe formed precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash-chromatography (SiO2, CH2Cl2/MeOH 98:2)

Sources & evidence

ORD record
ord-a0e18d74350b405ab6d34edde64c75da
Source dataset
uspto-grants-2007_04
Patent number
US07202238B2

Reaction notes

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