Toluene → (2e)-3-[4-Amino-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-7-yl]acrylic acid

HRID 17143

반응식

HRID 17143 반응식
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:24]=[CH:25]/[C:26]([O:28]C(C)(C)C)=[O:27])=[CH:4][N:3]=1.C1(C)C=CC=CC=1>ClCCl.FC(F)(F)C(O)=O>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:12]=[CH:13][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][CH:16]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27])=[CH:4][N:3]=1

참가 물질

5

반응물 2

HCID 1140TolueneHCID 69776505Tert-butyl (2e)-3-[4-amino-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-7-yl]acrylate

생성물 1

HCID 18450609(2e)-3-[4-Amino-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-7-yl]acrylic acid수율 128.7%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 6422Trifluoroacetic acid용매

실험 절차

A solution of Example 221B (1.5 g, 3.4 mmol) in dichloromethane and trifluoroacetic acid (10 mL) was stirred for 2 hours at ambient temperature, treated with toluene (200 mL), and concentrated to provide 1.7 g (100%) of the desired product as the trifluoroacetate salt. 1H NMR (DMSO-d6, 400 MHz) δ 8.42 (s, 1H), 7.95 (s, 1H), 7.76 (d, 1H), 7.54 (dd, 2H), 7.46 (dt, 2H), 7.21 (t, 1H), 7.16 (dd, 4H), 6.61 (d, 1H); 13C NMR (DMSO-d6, 100 MHz) δ 167.0, 159.0, 158.6, 157.6, 156.0, 148.8, 137.7, 137.5, 131.0, 130.1, 128.2, 127.6, 124.0, 120.3, 119.4, 119.2, 118.7, 115.7.

후처리

  1. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a049aa796dde429893543361460396a3
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737160B2

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