Bromoacetic Acid → HCID 59430591, compound

HRID 506072Notes

Reaction equation

HRID 506072 reaction equation
Br[CH2:2][C:3]([OH:5])=O.CCN=C=NCCCN(C)C.[ClH:17].[NH2:18][C:19]1[CH:20]=[C:21]([C:26]2[N:27]([CH2:39][CH3:40])[C:28]3[C:33]([C:34]=2[C:35]#[N:36])=[CH:32][CH:31]=[C:30]([O:37][CH3:38])[CH:29]=3)[CH:22]=[CH:23][C:24]=1[OH:25]>C(#N)C>[Cl:17][CH2:2][C:3]([NH:18][C:19]1[CH:20]=[C:21]([C:26]2[N:27]([CH2:39][CH3:40])[C:28]3[C:33]([C:34]=2[C:35]#[N:36])=[CH:32][CH:31]=[C:30]([O:37][CH3:38])[CH:29]=3)[CH:22]=[CH:23][C:24]=1[OH:25])=[O:5]

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59425699HCID 59425699, compound

Product 1

HCID 59430591HCID 59430591, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Bromoacetic acid (52 mg, 0.37 mmol) is combined with EDCI hydrochloride (62 mg, 0.4 mmol) and acetonitrile (900 μL) to form a homogeneous solution. 2-(3-Amino-4-hydroxyphenyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (100 mg, 0.33 mmol), prepared as in example 1BG, step B, is added to the solution. A thick paste soon forms. Another 1.1 mL of acetonitrile is added and the mixture is then stirred at room temperature for 2 hours. The reaction mixture is then partitioned between H2O and EtOAc. The organic layer is dried and concentrated. Purification by silica gel chromatography (4/1, CH2Cl2/EtOAc) yields 2-chloro-N-[5-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-2-hydroxyphenyl]acetamide (82 mg, 60%), compound 333, as a white solid.

Workup

  1. customto form a homogeneous solution
  2. additionis added to the solution
  3. customThe reaction mixture is then partitioned between H2O and EtOAc
  4. customThe organic layer is dried
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (4/1, CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-130f895db3b242f3acbeebf2684a54dd
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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