Benzoyl chloride → HCID 10660450, compound

HRID 401699Notes

Reaction equation

HRID 401699 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCN(CC)CC>C(Cl)Cl>[CH3:14][O:13][C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:2]([C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][CH2:4]2)=[O:12]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 534083041H-Indole-5-carboxylic acid, 2,3-dihydro-, methyl ester, hydrochloride (1:1)

Product 1

HCID 10660450HCID 10660450, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2,3-dihydro-1H-indole-5-carboxylate HCl salt 55a (64.1 mg, 0.3 mmol), and benzoyl chloride 1t (0.042 mL, 0.36 mmol) in CH2Cl2 (1 mL) was added Et3N (0.13 mL, 0.9 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 2 h. The resulting mixture was partitioned between CH2Cl2 and H2O. The organic solution was dried over Na2SO4 and concentrated. Purification of the residue by flash column chromatography (silica gel, 10-20% EtOAc/Heptanes) gave 55g (88 mg). MS m/z (M+H+) 282.0.

Workup

  1. customThe resulting mixture was partitioned between CH2Cl2 and H2O
  2. dry with materialThe organic solution was dried over Na2SO4
  3. concentrationconcentrated
  4. customPurification of the residue by flash column chromatography (silica gel, 10-20% EtOAc/Heptanes)

Sources & evidence

ORD record
ord-ebd35f4aacb34836a7305aacdb9f065c
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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