Carbon tetrabromide → HCID 68651040, compound

HRID 646762Notes

Reaction equation

HRID 646762 reaction equation
[NH2:1][C:2]1[C:3]([C:16]([NH:18][CH2:19][CH3:20])=[O:17])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14]O)[CH:9]=2)=[CH:6][N:7]=1.C(Br)(Br)(Br)[Br:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[NH2:1][C:2]1[C:3]([C:16]([NH:18][CH2:19][CH3:20])=[O:17])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][Br:22])[CH:9]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 68650646HCID 68650646, compound

Product 1

HCID 68651040HCID 68651040, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-amino-N-ethyl-6-[3-(hydroxymethyl)phenyl]pyrazine-2-carboxamide (566.1 mg, 1.0 eq) in dichloromethane (20 mL) were added carbon tetrabromide (749.8 mg, 1.1 eq), triphenylphosphine (600 mg, 1.1 eq) at ambient temperature. After being stirred for 7 h, the reaction mixture was partitioned with dichloromethane (10 mL×3), washed with brine. The organic layer was combined and dried over anhydrous magnesium sulfate. Filteration and concentration in vacuo gave a crude product. Purification by column chromatography afforded the 3-amino-6-[3-(bromomethyl)phenyl]-N-ethylpyrazine-2-carboxamide (534 mg, 77% yield): 1H NMR (400 MHz, DMSO-d6): δ 8.87 (m, 2H), 8.84 (s, 2H), 8.23 (m, 1H), 7.61 (bs, 1H), 7.45 (m, 1H), 4.77 (s, 2H), 3.38 (m, 2H), 1.16 (m, 3H).

Workup

  1. customthe reaction mixture was partitioned with dichloromethane (10 mL×3)
  2. washwashed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationFilteration and concentration in vacuo
  5. customgave a crude product
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-eb11924fd29c45b8a2fd0895147f8fdc
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Reaction notes

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