1,3-Dibromopropane → HCID 86683691, compound

HRID 1525681Notes

Reaction equation

HRID 1525681 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[CH2:8][CH2:9][CH2:10]Br.[C:12]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][C:24]2[CH:33]=[CH:32][C:27]([C:28]([NH:30][CH3:31])=[O:29])=[C:26]([F:34])[CH:25]=2)=[O:22])=[CH:16][C:15]=1[C:35]([F:38])([F:37])[F:36])#[N:13]>CN(C=O)C>[F:36][C:35]([F:37])([F:38])[C:15]1[CH:16]=[C:17]([N:20]2[CH2:10][CH2:9][CH2:8][N:23]([C:24]3[CH:33]=[CH:32][C:27]([C:28]([NH:30][CH3:31])=[O:29])=[C:26]([F:34])[CH:25]=3)[C:21]2=[O:22])[CH:18]=[CH:19][C:14]=1[C:12]#[N:13]

Participants

5

Reactant 3

HCID 80011,3-Dibromopropane2×HCID 11430Potassium Carbonate2×HCID 71694800HCID 71694800, compound

Product 1

HCID 86683691HCID 86683691, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

K2CO3 (109 mg, 0.79 mmol) and 1,3-dibromopropane (32 mkl, 0.32 mmol) were added to a solution of 4-[4-cyano-3-(trifluoromethyl)-phenylcarbamoylamino]-N-methyl-2-fluorobenzamide (100 mg, 0.26 mmol) 2 in DMF (2 ml). Mixture was stirred at 90° C. In 18 h another portion of K2CO3 (109 mg) and 1,3-dibromopropane (32 mkl) were added and stirring was continued at the same temperature. Addition was repeated by 2 more times. After the reaction was completed the mixture was evaporated in vacuo, the residue was dissolved in chloroform, washed with water, dried over Na2SO4, the solvent was evaporated. The product was isolated by colomn chromatography on SiO2 (eluent—AcOEt). LCMS (M+H)+ 421. 1H NMR (DMSO-d6, 400 MHz): 8.17 (br. m, 1H), 8.13 (d, J=8.4 Hz, 1H), 8.07 (d, J=2.0 Hz, 1H), 7.83 (dd, J1=8.4 Hz, J2=2.0 Hz, 1H), 7.62 (t, J=8.4 Hz, 1H), 7.38 (dd, J1=12.4 Hz, J2=2.0 Hz, 1H), 7.29 (dd, J1=8.4 Hz, J2=2.0 Hz, 1H), 3.90 (t, J=5.8 Hz, 2H), 3.81 (t, J=5.8 Hz, 2H), 2.77 (d, J=4.8 Hz, 3H), 2.21 (m, 2H).

Workup

  1. stirringstirring
  2. additionAddition
  3. customwas evaporated in vacuo
  4. dissolutionthe residue was dissolved in chloroform
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. customthe solvent was evaporated
  8. customThe product was isolated by colomn chromatography on SiO2 (eluent—AcOEt)

Sources & evidence

ORD record
ord-17cfeae8ee8847f1ae7e6bbf201313a6
Source dataset
uspto-grants-2015_07
Patent number
US09085539B2

Reaction notes

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