2-Bromoethanol → HCID 11583718, compound

HRID 734793Notes

Reaction equation

HRID 734793 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][OH:10].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]([C:24]#[C:25][C:26]3[CH:40]=[CH:39][C:29]([O:30][CH2:31][CH2:32][NH:33][CH:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)=[C:28]([CH3:41])[CH:27]=3)=[N:22][CH:23]=2)=[CH:14][CH:13]=1>CN(C=O)C>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:19]=[CH:20][C:21]([C:24]#[C:25][C:26]3[CH:40]=[CH:39][C:29]([O:30][CH2:31][CH2:32][N:33]([CH:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)[CH2:8][CH2:9][OH:10])=[C:28]([CH3:41])[CH:27]=3)=[N:22][CH:23]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 108982-Bromoethanol2×HCID 11430Potassium Carbonate2×HCID 11524800HCID 11524800, compound

Product 1

HCID 11583718HCID 11583718, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

55 mg (0.40 mmol) of potassium carbonate and 28 μL (0.40 mmol) of 2-bromoethanol was added to a solution of 86.2 mg (0.20 mmol) of (2-{4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethyl)cyclopentylamine in 2 mL of DMF and the mixture was stirred for 24 hours at RT. Another 55 mg (0.40 mmol) of potassium carbonate and 28 μL (0.40 mmol) of 2-bromoethanol were added and the mixture was stirred for 8 hours at 50° C. The reaction mixture was evaporated down in vacuo and the residue was taken up in DCM. The organic phase was washed with water, dried over sodium sulfate, and evaporated down in vacuo. The crude product was purified by MPLC (silica gel, EtOAc/MeOH 95:5) and then MPLC (Alox, cyc/EtOAc 8:2) and triturated with DIPE. Yield: 2.9 mg (3% of theoretical); C29H31ClN2O2 (M=475.021); calc.: molpeak (M+H)+: 475/477 (Cl); found: molpeak (M+H)+: 475/477 (Cl); Rf value: 0.26 (silica gel, EtOAc/MeOH 95:5)

Workup

  1. stirringthe mixture was stirred for 8 hours at 50° C
  2. customThe reaction mixture was evaporated down in vacuo
  3. washThe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated down in vacuo
  6. customThe crude product was purified by MPLC (silica gel, EtOAc/MeOH 95:5)
  7. customMPLC (Alox, cyc/EtOAc 8:2) and triturated with DIPE

Sources & evidence

ORD record
ord-e3cec2db3f764f1d81bee5110e2d81c7
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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