Dimethylacetamide → N-[1-Cyano-2-(4-cyano-6-trifluoromethyl-2H-benzotriazol-2-yl)-1-methylethyl]-4-trifluoromethoxybenzamide

HRID 70968

반응식

HRID 70968 반응식
Cl[C:2]1[C:10]2[C:6](=[N:7][N:8]([CH2:11][C:12]([NH:16][C:17](=[O:29])[C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)([C:14]#[N:15])[CH3:13])[N:9]=2)[CH:5]=[C:4]([C:30]([F:33])([F:32])[F:31])[CH:3]=1.C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C.C[C:64]([N:66](C)C)=O>[C-]#N.[Zn+2].[C-]#N.[Zn].FC(F)(F)C([O-])=O.[Pd+2].FC(F)(F)C([O-])=O>[C:14]([C:12]([NH:16][C:17](=[O:29])[C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=1)([CH3:13])[CH2:11][N:8]1[N:7]=[C:6]2[CH:5]=[C:4]([C:30]([F:31])([F:32])[F:33])[CH:3]=[C:2]([C:64]#[N:66])[C:10]2=[N:9]1)#[N:15]

참가 물질

7

반응물 3

HCID 31374DimethylacetamideHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 25122649N-[2-(4-Chloro-6-trifluoromethyl-2H-benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamide

생성물 1

HCID 86625572N-[1-Cyano-2-(4-cyano-6-trifluoromethyl-2H-benzotriazol-2-yl)-1-methylethyl]-4-trifluoromethoxybenzamide수율 63%

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 23994Zinc촉매HCID 2733347Palladium(II) trifluoroacetate촉매

실험 절차

N-[2-(4-Chloro-6-trifluoromethyl-2H-benzotriazol-2-yl)-1-cyano-1-methylethyl]-4-trifluoromethoxybenzamide (100 mg, described in Example 19), zinc cyanide (50 mg), zinc powder (10 mg), 2-di-t-butylphosphino-1,1′-binaphthyl (40 mg) and palladium trifluoroacetate (34 mg) were heated under nitrogen in degassed dimethylacetamide (1 mL) at 100° C. overnight. The mixture was concentrated under reduced pressure to give a residue that was purified by chromatography (SiO2, heptane/EA) to afford the title compound as a white solid (62 mg, 63%). Rf=0.6 (1:1 EA/heptane). MS (ES): M/Z [M+H]=483. NMR: (400 MHz, DMSO-d6): 1.77 (s, 3H), 5.56 (d, J=13.3 Hz, 1H), 5.66 (d, J=13.3 Hz, 1H), 7.49 (d, J=8.2 Hz, 2H), 7.92 (d, J=8.6 Hz, 2H), 8.59 (s, 1H), 8.90 (s, 1H) and 9.02 (s, 1H). 19F NMR (376 MHz, DMSO-d6): −61.0 (s, 3F) and −57.1 (s, 3F).

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give a residue that
  3. customwas purified by chromatography (SiO2, heptane/EA)

출처 및 근거

ORD 기록
ord-d1d7cea35fac48569757309e62d2b976
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822689B2

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