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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Potassium Carbonate → 3-(1,1-Dioxidotetrahydro-2H-thiopyran-4-yl)-5-[5-(hexahydro-1H-azepin-1-ylmethyl)-3-thienyl]-1H-indole-7-carboxamide

HRID 656088
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HRID 656088 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+].O1[CH2:49][CH2:48]OCC1>O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[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]5[CH2:49][CH2:48][CH2:3][CH2:4][CH2:5][CH2:6]5)[S:33][CH:34]=4)[CH:3]=3)[NH:7][CH:6]=2)[CH2:15][CH2:16]1
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참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 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 593328013-(1,1-Dioxidotetrahydro-2H-thiopyran-4-yl)-5-[5-(hexahydro-1H-azepin-1-ylmethyl)-3-thienyl]-1H-indole-7-carboxamide

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매

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온도
150 °C

실험 절차

To 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (100 mg, 0.27 mmol) in dioxane and water (3 mL/1 mL) was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarbaldehyde (116 mg), Pd(PPH3)4 (30 mg) and K2CO3 (112 mg). The reaction mixture was heated to 150° C. for 900 seconds by microwave irradiation. The organic phase was separated, concentrated, and redissolved in DMSO (3 mL). The resulting solution was split to two. NaBH3CN (30 mg), ZnCl2 (30 mg) and hexahydro-1H-azepine (50 mg) was added. The mixture was heated to 100° C. for 30 minutes which was then purified by HPLC with TFA to afford the title compound (13 mg).

후처리

  1. customThe organic phase was separated
  2. concentrationconcentrated
  3. dissolutionredissolved in DMSO (3 mL)
  4. customThe resulting solution was split to two
  5. additionNaBH3CN (30 mg), ZnCl2 (30 mg) and hexahydro-1H-azepine (50 mg) was added
  6. temperatureThe mixture was heated to 100° C. for 30 minutes which
  7. customwas then purified by HPLC with TFA

출처 및 근거

ORD 기록
ord-e731b87cadac413bb32c39538d14d7a1
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08071584B2

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