Bromoacetic Acid → HCID 59430591, compound

HRID 907172Notes

Reaction equation

HRID 907172 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) was 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, was added to the solution. A thick paste soon formed. Another 1.1 mL of acetonitrile was added and the mixture was then stirred at room temperature for 2 hours. The reaction mixture was then partitioned between H2O and EtOAc. The organic layer was dried and concentrated. Purification by silica gel chromatography (4/1, CH2Cl2/EtOAc) yielded 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. additionwas added to the solution
  3. customA thick paste soon formed
  4. customThe reaction mixture was then partitioned between H2O and EtOAc
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (4/1, CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-41395d7358734ce0b12940f479f7e261
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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