1,4-Dibromobutane → HCID 18516870, compound

HRID 1370090Notes

Reaction equation

HRID 1370090 reaction equation
[NH2:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:16]([C:17]#[N:18])=[CH:15][N:14]=[C:13]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][CH2:35][CH2:36][CH2:37]Br>CN(C=O)C>[C:17]([C:16]1[C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:2]([CH3:4])([N:1]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[CH3:3])=[CH:6][CH:7]=2)=[N:12][C:13]([NH:19][C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)=[N:14][CH:15]=1)#[N:18]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 18517016HCID 18517016, compound

Product 1

HCID 18516870HCID 18516870, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound (1.0 g,2.88 mmol) of Example 20 in DMF (20 mL) was added potassium carbonate (786 mg, 5.7 mmol) and 1,4-dibromobutane (622 mg, 2.88 mmol) and the resulting mixture stirred at 60° for 12 h. The reaction was partitioned between brine and ethyl acetate then the organic phase was dried (MgSO4) and concentrated under reduced pressure. The residue was subjected to column chromatography to give the title compound (591 mg) as a yellow solid, m.p. 124°. δH (d6 DMSO) 8.58 (1H, s), 7.94 (2H, dapp, J 8.4 Hz), 7.63 (4H, m), 6.96 (2H, tapp, J 8.7 Hz), 3.23 (4H, s), 2.61 (4H, s) and 1.47 (6H, s).

Workup

  1. customThe reaction was partitioned between brine and ethyl acetate
  2. dry with materialthe organic phase was dried (MgSO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a9bc6e8510a04a14a1392a4ef5717373
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Reaction notes

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