Indoline → HCID 22731926, compound

HRID 2083900Notes

Reaction equation

HRID 2083900 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][CH2:10]1.C(N(CC)C(C)C)(C)C>C(O)CCC>[Cl:1][C:2]1[N:7]=[C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10328IndolineHCID 775312,4-DichloropyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 22731926HCID 22731926, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 2,4-dichloropyrimidine (596 mg, 4.0 mmol), indoline (0.45 ml, 4.0 mmol) and N,N-diisopropylethylamine (0.69 ml, 4.0 mmol) in n-butanol (20 ml) was heated at 100° C. for 18 hours. Silica (3 g) was added and volatile material was removed by evaporation. The residue was purified by column chromatography, eluting with 0-40% ethyl acetate/isohexane, to give the product as a colourless solid (460 mg, 50%). NMR (CDCl3): 3.2 (t, 2H), 4.0-4.1 (t, 2H), 6.5 (d, 1H), 7.0-7.1 (m, 1H) 7.2-7.3 (m, 2H), 8.2 (m, 1H), 8.3-8.4 (m, 1H); MS (MH+): 232.7.

Workup

  1. additionSilica (3 g) was added
  2. customvolatile material was removed by evaporation
  3. customThe residue was purified by column chromatography
  4. washeluting with 0-40% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-58aaf6fb93cd4e57894f3b55942ac5a6
Source dataset
uspto-grants-2004_04
Patent number
US06716831B1

Reaction notes

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