Triethylamine → (2e)-3-[4-Amino-3-(3-phenoxy-1-propynyl)thieno[3,2-c]pyridin-7-yl]-n-methylacrylamide

HRID 17124

反応式

HRID 17124 の反応式
Br[C:2]1[C:6]2[C:7]([NH2:12])=[N:8][CH:9]=[C:10](I)[C:5]=2[S:4][CH:3]=1.[CH2:13]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14]#[CH:15].[CH:23]1[CH:28]=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:24]=1.CC[N:44]([CH2:47]C)CC.C[O:50]CCOC.O.C(O)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[NH2:12][C:7]1[C:6]2[C:2]([C:15]#[C:14][CH2:13][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:3][S:4][C:5]=2[C:10](/[CH:24]=[CH:23]/[C:28]([NH:44][CH3:47])=[O:50])=[CH:9][N:8]=1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 83613(Prop-2-ynyloxy)benzeneHCID 184507913-Bromo-7-iodothieno[3,2-C]pyridin-4-amineHCID 86587095Dimethoxyethane ethanol water

生成物 1

HCID 11739996(2e)-3-[4-Amino-3-(3-phenoxy-1-propynyl)thieno[3,2-c]pyridin-7-yl]-n-methylacrylamide収率 27%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒

実験手順

A mixture of Example 21A (150 mg, 0.48 mmol), (2-propynyloxy)benzene (0.13 mL, 0.96 mmol), PdCl2(PPh3)2 (17 mg, 0.024 mmol), PPh3 (15 mg, 0.057 mmol), CuI (3 mg), and Et3N (1 mL, 7.2 mmol) in DME/water/ethanol (70:30:20 mixture, 2 mL) was heated in a sealed vial to 125° C. for 25 minutes with stirring in a Smith Synthesizer microwave oven (at 300 W). The reaction mixture was concentrated and the residue was purified by HPLC using the conditions described in Example 21C to provide 47 mg (27% yield) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 2.71 (d, J=4.6 Hz, 3H), 5.18 (s, 2H), 6.50 (d, J=16.0 Hz, 1H), 6.91 (s, 2H), 7.00 (t, J=7.4 Hz, 1H), 7.08 (dd, J=8.8, 0.9 Hz, 2H), 7.35 (dd, J=8.8, 7.4 Hz, 2H), 7.52 (d, J=16.0 Hz, 1H), 8.10-8.13 (m, 2H), 8.14 (s, 1H); MS (ESI(+)) m/e 364.0 (M+H)+.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by HPLC

出典と根拠

ORDレコード
ord-e5a31fd4115d4791a984a247d56d9882
出典データセット
uspto-grants-2010_06
特許番号
US07737160B2

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