Water → HCID 69659198, compound

HRID 1829021Notes

Reaction equation

HRID 1829021 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=3)[NH:13][C:12]2=[O:21])=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:30][CH2:31][C:32](Cl)=[O:33].O>C1COCC1>[Cl:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:21])[C:11]2=[C:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][C:32](=[O:33])[CH:31]=[CH2:30])[CH:10]=2)[CH2:6][O:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 84944Propanoyl chloride, 3-bromo-HCID 684618673-(6-Amino-3H-isobenzofuran-1-ylidene)-5-chloro-1,3-dihydro-indol-2-one

Product 1

HCID 69659198HCID 69659198, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a stirred mixture of 3-(6-amino-3H-isobenzofuran-1-ylidene)-5-chloro-1,3-dihydro-indol-2-one (300 mg, 1.0 mmol) and triethylamine (0.41 ml, 3.0 mmol) in THF (10 ml), was added 3-bromopropionyl chloride (0.12 ml, 1.2 mmol). The mixture was heated at 45° C. for 2 hours, cooled to room temperature and poured into water (150 ml). The solid was filtered, washed with water and dried under vacuum to give crude product. The crude product was triturated with toluene to afforded N-[3-(5-chloro-2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-5-yl]-acrylamide as a bright yellow solid (315 mg, 89%).

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customdried under vacuum
  5. customto give crude product
  6. customThe crude product was triturated with toluene

Sources & evidence

ORD record
ord-4c4f43ecd55d4cc0ad954a727600db3f
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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