Indole-2-carboxylic acid → HCID 22676754, compound

HRID 1006246Notes

Reaction equation

HRID 1006246 reaction equation
N1[C:9]2[C:4](=[CH:5]C=CC=2)[CH:3]=C1C(O)=O.[Br:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15]=1[C:23]([OH:25])=[O:24].C(OC(OC(C)(C)C)N(C)C)(C)(C)C>C1(C)C=CC=CC=1>[Br:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15]=1[C:23]([O:25][C:4]([CH3:9])([CH3:5])[CH3:3])=[O:24]

Participants

5

Reactant 3

HCID 72899Indole-2-carboxylic acidHCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 23256883-bromo-1H-indole-2-carboxylic acid

Product 1

HCID 22676754HCID 22676754, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Indole-2-carboxylic acid was converted to 3-bromoindole-2-carboxylic acid using the method described for Example 13. N,N-dimethylformamide di-tert-butyl acetal (35 mL) was added dropwise to a stirring mixture of indole-3-bromo-2-carboxylic acid (14.9 g, 62 mmol) suspended in toluene (100 mL). After the addition was complete, the reaction was heated at 90° C. for 8 h. The reaction mixture was then cooled to room temperature and washed with cold water (2×100 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield the crude tert-butyl 3-bromoindole-2-carboxylate, assume quantitative yield. The crude product was used in the next step without purification.

Workup

  1. additionAfter the addition
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. washwashed with cold water (2×100 mL)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-86bb1b1400ff4981bb031d4cedf85771
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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