Carbon tetrabromide → HCID 12147027, compound

HRID 1836329Notes

Reaction equation

HRID 1836329 reaction equation
[F:1][C:2]([F:23])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:3][NH:4][C:5]1[C:6](=[O:16])[N:7]([CH2:12][CH2:13][CH2:14]O)[C:8]([CH3:11])=[CH:9][N:10]=1.C(Br)(Br)(Br)[Br:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[F:1][C:2]([F:23])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:3][NH:4][C:5]1[C:6](=[O:16])[N:7]([CH2:12][CH2:13][CH2:14][Br:25])[C:8]([CH3:11])=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 12147026HCID 12147026, compound

Product 1

HCID 12147027HCID 12147027, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred solution of 3-(2,2-difluoro-2-phenylethylamino)-1-(3-hydroxypropyl)-6-methylpyrazinone (2-12) (0.267 g, 0.82 mmol) and carbon tetrabromide (0.328 g, 0.99 mmol) in dichloromethane (10 mL), was added triphenylphosphine (0.26 g, 0.99 mmol) portionwise with ice-bath cooling. After the addition was complete, the mixture was stirred for an additional 2 hours. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography using ethyl acetate/n-hexane (2:1 to 1:1 gradient) as eluent to afford the title compound (0.309 g, 96.9%) as a yellow solid. Rf 0.45 ((EtOAc/hexane 1/1); 1H-NMR (CDCl3): δ 2.20 (d, J=1.2 Hz, 3H), 2.19-2.26 (m, 2H), 3.44 (t, J=6.4 Hz, 2H), 4.01-4.10 (m, 4H 6.12 (t, J=6.4 Hz, 1H), 6.62(d, J=1.2 Hz, 1H), 7.37-7.41 (m, 3H), 7.50-7.53 (m, 2H).

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. customThe solvent was removed in vacuo
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8cef669f60d94d509d707ec0c407108c
Source dataset
uspto-grants-2004_08
Patent number
US06777431B2

Reaction notes

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