Dichloromethane → (2,4-Dichloro-phenyl)(3-methyl-6-m-tolyl-benzofuran-2-yl)methanone

HRID 1443336

반응식

HRID 1443336 반응식
Br[C:2]1[CH:21]=[CH:20][C:5]2[C:6]([CH3:19])=[C:7]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=3[Cl:18])=[O:10])[O:8][C:4]=2[CH:3]=1.[CH3:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1.ClCCl.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[C:9]([C:7]1[O:8][C:4]2[CH:3]=[C:2]([C:27]3[CH:28]=[C:23]([CH3:22])[CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][C:5]=2[C:6]=1[CH3:19])=[O:10]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27339503-Tolylboronic acidHCID 59788907(6-Bromo-3-methyl-benzofuran-2-yl)(2,4-dichloro-phenyl)methanone

생성물 1

HCID 11280888(2,4-Dichloro-phenyl)(3-methyl-6-m-tolyl-benzofuran-2-yl)methanone수율 69.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 1140Toluene용매

반응 조건

온도
85 °C

실험 절차

A solution of (6-Bromo-3-methyl-benzofuran-2-yl)-(2,4-dichloro-phenyl)-methanone (50 mg, 0.13 mmol) in toluene (1.5 mL) and ethanol (1.5 mL) was degassed with argon for 15 min. At this time, 3-methyl benzene boronic acid (21.2 mg, 0.16 mmol, 1.2 eq) was added followed by [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II), complex with dichloromethane (1:1) (10.6 mg, 0.01 mmol, 0.1 eq) and 2M aqueous Na2CO3 (0.21 mL, 3 eq). The reaction was bubbled with argon for another 5 min and then heated to 85° C. for 4 h. The reaction was diluted with ethyl acetate, washed with water, brine, and dried over sodium sulfate. The solvent was removed at reduced pressure and purified on the pre-HPLC to afford 35.6 mg (69%) of a yellow solid as the product. 1H-NMR (CDCl3): δ 7.72 (d, J=8.0 Hz, 1H), 7.65 (s, 1H), 7.57 (dd, J=1.6, 8.0 Hz, 1H), 7.50 (d, J=1.9 Hz, 1H), 7.58 to 7.53 (m, 4H), 7.33 (t, 1H), 7.18 (d, J=7.2 Hz, 1H), 2.56 (s, 3H), 2.42 (s, 3H); LC-MS (MH+=395/397).

후처리

  1. customThe reaction was bubbled with argon for another 5 min
  2. additionThe reaction was diluted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed at reduced pressure
  6. custompurified on the pre-HPLC

출처 및 근거

ORD 기록
ord-f62fb26e70cc45f5ad70a33402c51fac
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659412B2

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