Indoline → HCID 59743394, compound

HRID 1946990Notes

Reaction equation

HRID 1946990 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1.C(N(CC)C(C)C)(C)C>CN(C=O)C.CCOC(C)=O>[CH3:9][S:8][C:4]1[N:3]=[C:2]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 10328IndolineHCID 81531DiisopropylethylamineHCID 971134-Chloro-2-methylthiopyrimidine

Product 1

HCID 59743394HCID 59743394, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-2-methylthiopyrimidine (4.02 g, 25 mmol), 2,3-dihydro-1H-indole (4.0 mL, 36 mmol) and N,N-diisopropyl ethyl amine (4 mL, 22 mmol) in DMF (10 mL) was heated to 100° C. under N2 for 16 h. The solidified reaction mixture was cooled, diluted with EtOAc, and filtered. The collected solids were dissolved in DCM and MeOH and recrystallized from DCM/EtOAc to give 1-(2-methylsulfanyl-pyrimidin-4-yl)-2,3-dihydro-1H-indole (2.32 g, 38% yield) as a light-yellow solid. MS=244[M+H]+.

Workup

  1. customThe solidified reaction mixture
  2. temperaturewas cooled
  3. filtrationfiltered
  4. dissolutionThe collected solids were dissolved in DCM
  5. customMeOH and recrystallized from DCM/EtOAc

Sources & evidence

ORD record
ord-d67f03d4f8ba48d7bc30cb02fa50bb22
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

Loading…