Sodium Carbonate → HCID 86724256, compound

HRID 873714Notes

Reaction equation

HRID 873714 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:38](=[CH:39][CH:40]=2)[O:37][CH2:36][C:32]2([CH2:35][O:34][CH2:33]2)[C:12]23[CH2:16][O:15][C:14]([N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[N:13]2)O1.Br[C:43]1[CH:44]=[N:45][CH:46]=[C:47]([C:49]#[C:50][CH2:51][O:52][CH3:53])[CH:48]=1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>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.O>[CH3:53][O:52][CH2:51][C:50]#[C:49][C:47]1[CH:48]=[C:43]([C:9]2[CH:10]=[C:11]3[C:38](=[CH:39][CH:40]=2)[O:37][CH2:36][C:32]2([CH2:35][O:34][CH2:33]2)[C:12]23[CH2:16][O:15][C:14]([N:17]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[C:25]([O:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[O:26])=[N:13]2)[CH:44]=[N:45][CH:46]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 22503122HCID 22503122, compoundHCID 86724247HCID 86724247, compound

Product 1

HCID 86724256HCID 86724256, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×

Conditions

Temperature
110 °C

Procedure

Under argon atmosphere, a mixture of di-tert-butyl [6′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl]imidodicarbonate (213 mg, 0.372 mmol), 3-bromo-5-(3-methoxyprop-1-yn-1-yl)pyridine (252 mg, 1.12 mmol), Na2CO3 (158 mg, 1.49 mmol), tetrakis(triphenylphosphine)palladium(0) (21.5 mg, 0.019 mmol), dioxane (3.4 mL) and water (0.85 mL) was stirred for 3 hours at 110° C. The reaction mixture was cooled down to ambient temperature, and water was added to the mixture. The mixture was extracted with MeOH—CHCl3 (1:9), and the organic layer was dried over Na2SO4 prior to filtration. The filtrate was concentrated at reduced pressure to give crude di-tert-butyl {6′-[5-(3-methoxyprop-1-yn-1-yl)pyridin-3-yl]dispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-yl}imidodicarbonate, which was used for the next reaction without further purification.

Workup

  1. temperatureThe reaction mixture was cooled down to ambient temperature
  2. extractionThe mixture was extracted with MeOH—CHCl3 (1:9)
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationto filtration
  5. concentrationThe filtrate was concentrated at reduced pressure

Sources & evidence

ORD record
ord-11e42407b1604454965225a41b5ace39
Source dataset
uspto-grants-2015_03
Patent number
US08975415B2

Reaction notes

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