Potassium Carbonate → 5-[3-({[(1S)-1,2-Dimethylpropyl]amino}methyl)phenyl]-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide

HRID 656096

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.[CH:22]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)=O.C([O-])([O-])=O.[K+].[K+].[BH3-]C#N.[Na+].[CH3:43][CH:44]([CH3:48])[C@@H:45]([NH2:47])[CH3:46]>O1CCOCC1.O.CS(C)=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.[Cl-].[Zn+2].[Cl-]>[CH3:46][C@H:45]([NH:47][CH2:22][C:24]1[CH:25]=[C:26]([C:2]2[CH:3]=[C:4]3[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=2)[NH:7][CH:6]=[C:5]3[CH:14]2[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH2:16][CH2:15]2)[CH:27]=[CH:28][CH:29]=1)[CH:44]([CH3:48])[CH3:43]

参加物

反応条件

温度: 100 °C

実験手順

To 5-bromo-3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxamide (80 mg, 0.216 mmol) in dioxane and water (4 mL/1 mL) was added (3-formylphenyl)boronic acid (45 mg), Pd(PPh3)4 (25 mg) and K2CO3 (104 mg). The reaction mixture was redissolved in DMSO (2 mL). To the resultant mixture zinc chloride (30 mg), NaCNBH3 (30 mg) and (2s)-3-methyl-2-butanamine (50 mg) were added. The mixture was heated to 100° C. for 30 minutes by microwave irradiation and purified by HPLC with TFA to afford the title compound (16 mg).

後処理

custompurified by HPLC with TFA

出典と根拠

ORDレコード: ord-1cd909fa55e74deea38760edf410ee6c
出典データセット: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08071584B2

反応式

参加物

反応物 5

生成物 1

試薬・触媒・溶媒 5

反応条件

実験手順

後処理

出典と根拠

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