Dichloromethane → 5-[7-(1-methyl-cyclohexanecarbonyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid

HRID 547482노트

반응식

HRID 547482 반응식
OB(O)[C:3]1[S:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1.Br[C:13]1[N:14]=[C:15]2[C:21]([C:22]([C:24]3([CH3:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:23])=[CH:20][N:19]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:16]2=[N:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:30][C:24]1([C:22]([C:21]2[C:15]3[C:16](=[N:17][CH:18]=[C:13]([C:3]4[S:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=4)[N:14]=3)[N:19]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:36])([CH3:38])[CH3:37])[CH:20]=2)=[O:23])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

참가 물질

8

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27798075-Boronothiophene-2-carboxylic acidHCID 57829583[2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-(1-methyl-cyclohexyl)-methanone

생성물 1

HCID 578295975-[7-(1-methyl-cyclohexanecarbonyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid수율 50.6%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 5-(dihydroxyboryl)-2-thiophene-carboxylic acid (1.0 g, 5.4 mmol), [2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-(1-methyl-cyclohexyl)-methanone (2.2 g, 4.9 mmol), potassium carbonate (2.0 g, 15 mmol), and Pd(dppf)Cl2.CH2Cl2 (0.400 g, 0.489 mmol) in 12 mL of 1,4-dioxane and 3 mL of water was stirred at 120° C. in a microwave for 40 min. The resulting red suspension was partitioned between 60 mL of ethyl acetate and 100 mL of water, and the aqueous layer was extracted with three 60 mL portions of ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated to a residue. Column chromatography (0->50% EtOAc/hexanes) afforded 1.24 g (46%) of 5-[7-(1-methyl-cyclohexanecarbonyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid as a brown solid.

후처리

  1. customThe resulting red suspension was partitioned between 60 mL of ethyl acetate and 100 mL of water
  2. extractionthe aqueous layer was extracted with three 60 mL portions of ethyl acetate
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a residue

출처 및 근거

ORD 기록
ord-e2c4f2cf268a4717a933f22b82635a9a
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939531B2

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