Iodine → Ethyl 2-(6-chloro-4-(isopropylamino)pyridin-3-yl)-5-methyloxazole-4-carboxylate

HRID 595483Notes

Reaction equation

HRID 595483 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([NH:20][CH:21]([CH3:23])[CH3:22])[C:5]([C:6]([NH:8][CH:9]([C:15](=[O:17])[CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=O)=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]2[O:17][C:15]([CH3:16])=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:8]=2)=[C:18]([NH:20][CH:21]([CH3:23])[CH3:22])[CH:19]=1

Participants

6

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 89689546Ethyl 2-(6-chloro-4-(isopropylamino)nicotinamido)-3-oxobutanoate

Product 1

HCID 89689612Ethyl 2-(6-chloro-4-(isopropylamino)pyridin-3-yl)-5-methyloxazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of ethyl 2-(6-chloro-4-(isopropylamino)nicotinamido)-3-oxobutanoate (27a) (200 mg, 0.58 mmol) in DCM (10 mL), triphenyl phosphine (2 equiv.), iodine (2 equiv.) and triethyl amine (3 equiv.) were added and stirred at room temperature for 4 h. The reaction mixture was diluted using DCM and washed with water. The organic layer was collected, dried over Na2SO4, filtered and concentrated. The crude material obtained was purified by column chromatography using silica gel and EtOAc:Pet. Ether as eluent to obtain the title compound, ethyl 2-(6-chloro-4-(isopropylamino)pyridin-3-yl)-5-methyloxazole-4-carboxylate. 1H NMR: 400 MHz, DMSO-d6: δ 1.25 (d, J=6.40 Hz, 6H), 1.33 (t, J=7.20 Hz, 3H), 2.67 (s, 3H), 3.90-3.95 (m, 1H), 4.31 (q, J=7.20 Hz, 2H), 6.89 (s, 1H), 8.47 (d, J=7.60 Hz, 1H), 8.54 (s, 1H).

Workup

  1. additionThe reaction mixture was diluted
  2. washwashed with water
  3. customThe organic layer was collected
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-92bcf9701d0749dea13d082d5aabde82
Source dataset
uspto-grants-2016_01
Patent number
US09242976B2

Reaction notes

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