Sodium Carbonate → HCID 18755933, compound

HRID 1385873Notes

Reaction equation

HRID 1385873 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]([O:34][CH2:35][CH:36]([CH3:38])[CH3:37])=[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]([O:34][CH2:35][CH:36]([CH3:38])[CH3:37])=[N:32][CH:33]=3)=[CH:16][CH:15]=2)[N:13]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 11046011HCID 11046011, compoundHCID 18755931HCID 18755931, compound

Product 1

HCID 18755933HCID 18755933, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 19096565Water ethanolSolvent

Procedure

2-(2,6-Difluorophenyl)-4-(4-bromophenyl)oxazoline (1.00 g, 2.96 mmol) was mixed with 5,5-dimethyl-2-(2-isobutyloxypyridin-5-yl)-1,3,2-dioxaborinane (1.4 g, purity 80%, 4.3 mmol), Pd(PPh3)4 (0.17 g, 0.15 mmol) and sodium carbonate (0.62 g, 5.9 mmol) in tolune/ethanol/water 8:2:1 (15 ml) and refluxed for 8 hours under nitrogen. After extraction and chromatography, 2-(2,6-difluorophenyl)-4-[4-(2-isobutyloxypyridin-5-yl)phenyl]oxazoline was obtained, 1.14 g, colorless oil.

Workup

  1. temperaturerefluxed for 8 hours under nitrogen
  2. extractionAfter extraction and chromatography

Sources & evidence

ORD record
ord-c97b180ea3b4486195edc0ceaa5f6e08
Source dataset
uspto-grants-2001_07
Patent number
US06265350B1

Reaction notes

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