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

HRID 17124

반응식

HRID 17124 반응식
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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-e5a31fd4115d4791a984a247d56d9882
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737160B2

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