Sodium Carbonate → 6'-(4-Methoxypyridin-2-yl)-2',2'-dimethyldispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-amine

HRID 594904

반응식

HRID 594904 반응식
C(OC([N:8]([C:16]1[O:17][CH2:18][C:19]2([N:43]=1)[C:28]1([CH2:31][O:30][CH2:29]1)[C:27]([CH3:33])([CH3:32])[O:26][C:25]1[C:20]2=[CH:21][C:22](B2OC(C)(C)C(C)(C)O2)=[CH:23][CH:24]=1)C(OC(C)(C)C)=O)=O)(C)(C)C.Br[C:45]1[CH:50]=[C:49]([O:51][CH3:52])[CH:48]=[CH:47][N:46]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.CO.C(Cl)(Cl)Cl.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>[CH3:52][O:51][C:49]1[CH:48]=[CH:47][N:46]=[C:45]([C:22]2[CH:21]=[C:20]3[C:25](=[CH:24][CH:23]=2)[O:26][C:27]([CH3:32])([CH3:33])[C:28]2([CH2:29][O:30][CH2:31]2)[C:19]23[CH2:18][O:17][C:16]([NH2:8])=[N:43]2)[CH:50]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 47384842-Bromo-4-methoxypyridineHCID 86724310Di-tert-butyl[2',2'-dimethyl-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

생성물 1

HCID 867243096'-(4-Methoxypyridin-2-yl)-2',2'-dimethyldispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-amine수율 81.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 21584188Chloroform methanol용매HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
100 °C

실험 절차

A mixture of di-tert-butyl[2′,2′-dimethyl-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 (282 mg, 0.470 mmol), 2-bromo-4-methoxypyridine (221 mg, 1.17 mmol), tetrakis(triphenylphosphine)palladium(0) (271 mg, 0.235 mmol) and Na2CO3 (149 mg, 1.41 mmol) in dioxane-water (4:1, 5.6 mL) was stirred for 8 hours at 100° C. The mixture was diluted with MeOH—CHCl3 (1:9) and washed with water, then the organic layer was dried over MgSO4 and filtered. The filtrate was concentrated at reduced pressure. To the residue were added toluene (2.8 mL) and silica gel (neutral; 846 mg), and the mixture was stirred for 3 hours at 120° C. After concentration of the reaction mixture at reduced pressure, the residue was purified with column chromatography on silica gel (CHCl3-EtOH, a linear gradient of EtOH from 0 to 20%) afforded 6′-(4-methoxypyridin-2-yl)-2′,2′-dimethyldispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-amine (146 mg).

후처리

  1. washwashed with water
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated at reduced pressure
  5. additionTo the residue were added toluene (2.8 mL) and silica gel (neutral; 846 mg)
  6. stirringthe mixture was stirred for 3 hours at 120° C
  7. customAfter concentration of the reaction mixture at reduced pressure, the residue was purified with column chromatography on silica gel (CHCl3-EtOH

출처 및 근거

ORD 기록
ord-8199f9467c6b4c2ca6947f5719e882f1
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242973B2

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