Indoline → (2-Chloropyridin-4-yl)-(2,3-dihydroindol-1-yl)-methanone

HRID 74507

Reaction equation

HRID 74507 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][N:19]=1)[C:14](O)=[O:15].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C1COCC1.C(OCC)(=O)C>[Cl:10][C:11]1[CH:12]=[C:13]([C:14]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)=[O:15])[CH:17]=[CH:18][N:19]=1

Participants

7

Reactant 4

HCID 10328IndolineHCID 81531DiisopropylethylamineHCID 2369852-Chloroisonicotinic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 28376039(2-Chloropyridin-4-yl)-(2,3-dihydroindol-1-yl)-methanone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

400 μL (3.53 mmol) 2,3-dihydro-1H-indole were added to 500 mg (3.17 mmol) 2-chloroisonicotinic acid, 600 μL (3.49 mmol) DIPEA and 1.10 g (3.43 mmol) TBTU in 20 mL THF. The reaction mixture was stirred overnight, diluted with ethyl acetate and washed with 15% potassium carbonate solution (1×), water (1×) and 1M hydrochloric acid (1×). The organic phase was dried on magnesium sulphate, filtered and evaporated down i. vac. The residue was triturated with diisopropylether and suction filtered. The solid was dried at 40° C. in the circulating air dryer.

Workup

  1. washwashed with 15% potassium carbonate solution (1×), water (1×) and 1M hydrochloric acid (1×)
  2. customThe organic phase was dried on magnesium sulphate
  3. filtrationfiltered
  4. customevaporated down i
  5. customThe residue was triturated with diisopropylether and suction
  6. filtrationfiltered
  7. customThe solid was dried at 40° C. in the circulating air dryer

Sources & evidence

ORD record
ord-f7906a4de1474d21a55b05796cf0e145
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

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