Lithium Chloride → HCID 58592807, compound

HRID 642862Notes

Reaction equation

HRID 642862 reaction equation
Br[C:2]1[CH:11]=[N:10][C:5]2=[N:6][CH:7]=[CH:8][N:9]=[C:4]2[CH:3]=1.[CH2:12](C([Sn])=C(CCCC)CCCC)[CH2:13]CC.[Li+].[Cl-]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:12]([C:2]1[CH:11]=[N:10][C:5]2=[N:6][CH:7]=[CH:8][N:9]=[C:4]2[CH:3]=1)=[CH2:13]

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 42469437-bromopyrido[2,3-b]pyrazineHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 58592807HCID 58592807, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

7-Bromo-pyrido[2,3-b]pyrazine (560 mg, 2.7 mmol) was suspended in toluene (25 ml) with tributylvinyltin (2.30 ml, 8.1 mmol), tetrakis(triphenylphosphine) palladium (106 mg, 106 mmol) and LiCl (336 mg, 8.06 mmol). The mixture was heated to 100° C. under a nitrogen atmosphere. After 2 h, the reaction was complete and the toluene was removed under vacuum. The crude was taken up in ethyl acetate and washed three times with a 1 N HCl solution. The combined acid washings were washed twice with ethyl acetate. The acidic water was made basic with the addition of solid sodium carbonate, and extracted three times with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried using MgSO4, and concentrated under vacuum to yield the title product (250 mg, 59%) as a tan solid.1H NMR (DMSO-d6): δ=9.40 (d, 1H, J=2.5Hz), 9.08 (dd, 2H, J=12.3 Hz, 1.8 Hz), 8.60 (d, 1H, J=2.5 Hz), 7.11(m,1H), 6.40 (d, 1H, J=17.8 Hz,), 5.64 (d, 1H, J=11.3 Hz). Calculated mass=157.18, [M+H]+=158. HPLC Method D: 99.3% @ 210-370 nm; 99.7% @ 240 nm; RT=4.5 min.

Workup

  1. customthe toluene was removed under vacuum
  2. washwashed three times with a 1 N HCl solution
  3. washThe combined acid washings were washed twice with ethyl acetate
  4. additionThe acidic water was made basic with the addition of solid sodium carbonate
  5. extractionextracted three times with ethyl acetate
  6. washThe combined ethyl acetate extracts were washed with brine
  7. customdried
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5526a247674f49f2aace80674d6ecbb2
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Reaction notes

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