Tributylamine → HCID 22033734, compound

HRID 1791880Notes

Reaction equation

C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8](Br)[CH:7]=[CH:6][C:5]=1[NH:11][C:12](=[O:15])[CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].C(N(CCCC)CCCC)CCC.[F:36][C:37]1[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=1[CH:39]=[CH2:40].[OH-].[Na+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[F:36][C:37]1[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=1/[CH:39]=[CH:40]/[C:8]1[CH:7]=[CH:6][C:5]([NH:11][C:12](=[O:15])[CH2:13][CH3:14])=[C:4]([CH:9]=1)[C:3]([OH:2])=[O:16]

Participants

Conditions

Temperature: 150 °C

Procedure

To a mixture of 5-bromo-2-propionylamino-benzoic acid methyl ester (1.0 g, 3.50 mmol), potassium carbonate (532 mg, 3.85 mmol), tri-n-butyl amine (0.917 mL, 3.85 mmol) and PdCl2(PPh3)2 (35 mg, 0.05 mmol) in DMF (20 mL) was added 2-fluoro-styrene (0.50 mL, 4.2 mmol). The reaction mixture was heated to 150° C. and left at this temperature for 18 hours. after which it was allowed to reach room temperature. Water (10 mL) and 5M NaOH (2 mL) were added and the temperature was once again raised to 150° C. After one hour at this temperature the reaction mixture was allowed to reach room temperature. Water (50 mL) was added and the mixture was filtered by suction through Celite. The filtrate was acidified with 5M HCl, the product collected by filtration and re-crystallised from ethanol (511 mg, 47%).

Workup

customto reach room temperature
temperaturethe temperature was once again raised to 150° C
waitAfter one hour at this temperature the reaction mixture was allowed
customto reach room temperature
filtrationthe mixture was filtered by suction through Celite
filtrationthe product collected by filtration
customre-crystallised from ethanol (511 mg, 47%)

Sources & evidence

ORD record: ord-e1a1e104cb264a8a82da99664cd0d420
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074831B2

Reaction notes

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