Sodium Carbonate → HCID 18755937, compound

HRID 1385875Notes

Reaction equation

HRID 1385875 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[N:13]=1.CC1(C)COB([C:28]2[CH:29]=[CH:30][C:31]([CH2:34][CH2:35][CH3:36])=[N:32][CH:33]=2)OC1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[O:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([C:28]3[CH:29]=[CH:30][C:31]([CH2:34][CH2:35][CH3:36])=[N:32][CH:33]=3)=[CH:16][CH:15]=2)[N:13]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 11046011HCID 11046011, compoundHCID 131722781HCID 131722781, compound

Product 1

HCID 18755937HCID 18755937, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 19096565Water ethanolSolvent

Procedure

2-(2,6-Difluorophenyl)4-(4-bromophenyl)oxazoline (0.8 g, 2.4 mmol) was refluxed for 8 hours with dimethyl-2-(2-n-propylpyridin-5-yl)-1,3,2-dioxaborinane (0.72 g, 3.1 mmol), Pd(PPh3)4 (0.14 g, 0.12 mmol) and sodium carbonate (0.5 g) in tolune/ethanol/water 8:2:1 (11 ml). After extraction and chromatography, 2-(2,6-difluorophenyl)4-[4-(2-n-propylpyridin-5-yl)phenyl]oxazoline was obtained, 0.20 g, pale solid.

Workup

  1. extractionAfter extraction and chromatography

Sources & evidence

ORD record
ord-63ba322cd6aa4c1d97f405447d6fad7e
Source dataset
uspto-grants-2001_07
Patent number
US06265350B1

Reaction notes

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