2,3,4-Trifluorobenzoic acid → 3,4-Difluoro-2-[[2-fluoro-4-(ethylthio)phenyl]amino]benzoic acid

HRID 1793044노트

반응식

HRID 1793044 반응식
F[C:2]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:13][C:14]1[CH:20]=[C:19]([S:21][CH2:22][CH3:23])[CH:18]=[CH:17][C:15]=1[NH2:16].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[F:11][C:10]1[C:2]([NH:16][C:15]2[CH:17]=[CH:18][C:19]([S:21][CH2:22][CH3:23])=[CH:20][C:14]=2[F:13])=[C:3]([CH:7]=[CH:8][C:9]=1[F:12])[C:4]([OH:6])=[O:5]

참가 물질

5

반응물 3

HCID 3029322,3,4-Trifluorobenzoic acidHCID 2733832Lithium HexamethyldisilazideHCID 220256792-Fluoro-4-ethylthioaniline2회

생성물 1

HCID 220256913,4-Difluoro-2-[[2-fluoro-4-(ethylthio)phenyl]amino]benzoic acid수율 55%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2,3,4-Trifluorobenzoic acid and the product of Example 27, Step A, 2-fluoro-4-ethylthioaniline, were reacted in the presence of LiHMDS solution in THF by the general procedure of Example 1, Step B. After workup, a yellow solid was obtained which was purified by dry flash column chromatography on silica (0.5% Et2O in 1:1 CH2Cl2/hexanes as eluant) to afford 3,4-difluoro-2-[[2-fluoro-4-(ethylthio)phenyl]amino]benzoic acid as a yellow solid (55%); m.p. (Et2O) 136–139° C. 1H NMR (400 MHz, CDCl3) δ 13.70 (br s, 1 H), 9.24 (br s, 1 H), 7.81 (ddd, J=9.2, 6.1, 2.1 Hz, 1 H), 7.26 (dd, J=11.8, 2.0 Hz, 1 H), 7.08 (dd, J=8.3, 2.0 Hz, 1 H), 7.06 (td, J=9.7, 7.0 Hz, 1 H), 7.02 (ddd, J=9.2, 8.3, 4.7 Hz, 1 H), 2.96 (q, J=7.3 Hz, 2 H), 1.22 (t, J=7.3 Hz, 3 H). Anal. Calcd for C15H12F3NO2S: C, 55.0; H, 3.7; N, 4.3. Found: C, 55.5; H, 3.7; N, 4.3.

후처리

  1. customAfter workup, a yellow solid was obtained which
  2. customwas purified
  3. customby dry flash column chromatography on silica (0.5% Et2O in 1:1 CH2Cl2/hexanes as eluant)

출처 및 근거

ORD 기록
ord-abfaeb570e064d149175c8c236dc2def
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07078438B2

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