Potassium Carbonate → 3-(1,1-Dioxidotetrahydro-2H-thiopyran-4-yl)-5-(5-{[methyl(1-methylethyl)amino]methyl}-3-thienyl)-1H-indole-7-carboxamide

HRID 387328노트

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HRID 387328 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH2:16][CH2:15]1.CC1(C)C(C)(C)OB([C:30]2[CH:31]=[C:32]([CH:35]=O)[S:33][CH:34]=2)O1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.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:20]=[S:17]1(=[O:21])[CH2:18][CH2:19][CH:14]([C:5]2[C:4]3[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=[C:2]([C:30]4[CH:31]=[C:32]([CH2:35][N:7]([CH3:6])[CH:8]([CH3:9])[CH3:4])[S:33][CH:34]=4)[CH:3]=3)[NH:7][CH:6]=2)[CH2:15][CH2:16]1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 467397834-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carbaldehydeHCID 593327575-Bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide

생성물 1

HCID 593327473-(1,1-Dioxidotetrahydro-2H-thiopyran-4-yl)-5-(5-{[methyl(1-methylethyl)amino]methyl}-3-thienyl)-1H-indole-7-carboxamide수율 4.8%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
150 °C

실험 절차

To 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (400 mg, 1.08 mmol) in dioxane and water (4 mL/1 mL) was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarbaldehyde (462 mg), Pd(PPh3)4 (100 mg) and K2CO3 (447 mg). The reaction mixture was heated to 150° C. for 20 minutes in microwave. The organic phase was concentrated and redissolved in DMSO (10 mL). The resulting solution was split to eight. NaBH3CN (30 mg), ZnCl2 (30 mg) and N-methyl-2-propanamine (50 mg) were added. The mixture was heated at 100° C. for 30 minutes which was then filtered and purified by HPLC with TFA to afford the title compound (12 mg).

후처리

  1. concentrationThe organic phase was concentrated
  2. dissolutionredissolved in DMSO (10 mL)
  3. customThe resulting solution was split to eight
  4. additionNaBH3CN (30 mg), ZnCl2 (30 mg) and N-methyl-2-propanamine (50 mg) were added
  5. temperatureThe mixture was heated at 100° C. for 30 minutes which
  6. filtrationwas then filtered
  7. custompurified by HPLC with TFA

출처 및 근거

ORD 기록
ord-6f1f48c783e345fda2150d33991c480e
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372875B2

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