2-Bromo-1-(4-fluorophenyl)ethan-1-one → HCID 21978430, 화합물

HRID 10215

반응식

HRID 10215 반응식
Cl.[NH:2]1[CH2:5][CH:4]([CH2:6][S:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:3]1.Br[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)=[O:21]>>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C:20](=[O:21])[CH2:19][N:2]2[CH2:5][CH:4]([CH2:6][S:7]([C:10]3[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=3)(=[O:9])=[O:8])[CH2:3]2)=[CH:23][CH:24]=1

참가 물질

3

반응물 2

HCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 21978414HCID 21978414, 화합물

생성물 1

HCID 21978430HCID 21978430, 화합물수율 29%

실험 절차

Following the procedure of Example 2, 4-[(azetidin-3-ylmethyl)sulfonyl]benzonitrile hydrochloride (75 mg, 0.27 mmol) was reacted with 2-bromo-1-(4-fluorophenyl)ethanone. Crude product was purified on a 10 g bond elute silica cartridge using the personal flash master eluting with 0.5% MeOH/DCM to 2% MeOH/DCM to give the freebase as a pale yellow gum (30 mg, 29%). The freebase was dissolved in 3:1 ether/MeOH (5 ml) and 1.0M hydrogen chloride in ether (89μl) was added. The side of the flask was etched and the salt precipitated and was isolated by filtration and dried under vacuum to give the title compound as a white solid (20 mg). 1H NMR (500 MHz, CDCl3) δ 3.05–3.13 (1H, m), 3.90–3.96 (2H, m), 4.03–4.12 (2H, m), 4.23–4.30 (2H, m), 5.06 (2H, s), 7.44 (2H, t, J=8.8 Hz), 8.01 (2H, dd, J=5.4 & 8.8 Hz), 8.09 (2H, d, J=8.6 Hz), 8.21 (2H, d, J=8.6 Hz), 10.62 (1H, s). m/z (ES+) 373 (M+H)+.

후처리

  1. customCrude product was purified on a 10 g bond
  2. washelute silica cartridge
  3. washeluting with 0.5% MeOH/DCM to 2% MeOH/DCM

출처 및 근거

ORD 기록
ord-945dc99b109345e4a9e046f358d68973
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094777B2

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