Potassium Carbonate → tert-Butyl 4-[2-phenyl-1-(phenylsulfonyl)-1H-indol-4-yl]-1-piperazinecarboxylate

HRID 8341

反応式

I[C:2]1[N:3]([S:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)(=[O:26])=[O:25])[C:4]2[C:9]([CH:10]=1)=[C:8]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)[CH:7]=[CH:6][CH:5]=2.[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C([O-])([O-])=O.[K+].[K+]>C(COC)OC.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>[C:33]1([C:2]2[N:3]([S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:25])=[O:26])[C:4]3[C:9]([CH:10]=2)=[C:8]([N:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:15][CH2:16]2)[CH:7]=[CH:6][CH:5]=3)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

参加物

実験手順

tert-Butyl 4-[2-iodo-1-(phenylsulfonyl)-1H-indol-4-yl]-1-piperazinecarboxylate(40 mg, 0.07 mmol), phenyl boronic acid (12 mg, 0.1 mmol), Pd(PPh3)4 (2 mg, 0.002 mmol) and a 2M aqueous solution of K2CO3 (0.075 mL) were stirred for 3 days at 80° C. in dimethoxyethane (2 mL). After evaporation of the solvent, the crude was purified by column chromatography (SiO2) and led to 30 mg of the desired compound (80%). 1H NMR (270 MHz, DMSO-d6) δ 8.02 (d, J=8 Hz, 1 H), 7.55–7.20 (in, 11 H), 6.78 (t, J=8 Hz, 1 H), 7.57 (s, 1 H), 3.58 (in, 4 H), 3.02 (in, 4 H), 1.48 (in, 9 H). MS (ESI+) for m/z 518 (M+H)+.

後処理

customAfter evaporation of the solvent
customthe crude was purified by column chromatography (SiO2)

出典と根拠

ORDレコード: ord-126fbc52cb0b4e498ab0321d2c86dc56
出典データセット: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07087750B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 2

実験手順

後処理

出典と根拠

関連ノート