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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
ノート
印刷プレビュー

反応式

HRID 656088 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒

反応条件

温度
150 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e731b87cadac413bb32c39538d14d7a1
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08071584B2

反応ノート

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