N,N,N',N'-Tetramethylazodicarboxamide → Ethyl[4-(2-{5-[bis(4-fluorophenyl)methyl]-2-oxopyridin-1(2h)-yl}ethoxy)-2-methyl-1h-benzimidazol-1-yl]acetate

HRID 2389327노트

반응식

HRID 2389327 반응식
[OH:1][C:2]1[C:10]2[N:9]=[C:8]([CH3:11])[N:7]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)[C:26]2[CH:27]=[CH:28][C:29](=[O:35])[N:30]([CH2:32][CH2:33]O)[CH:31]=2)=[CH:21][CH:20]=1.N(C(N(C)C)=O)=NC(N(C)C)=O.C(P(CCCC)CCCC)CCC>C1COCC1.C1(C)C=CC=CC=1>[CH2:16]([O:15][C:13](=[O:14])[CH2:12][N:7]1[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([O:1][CH2:33][CH2:32][N:30]3[CH:31]=[C:26]([CH:25]([C:22]4[CH:21]=[CH:20][C:19]([F:18])=[CH:24][CH:23]=4)[C:36]4[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=4)[CH:27]=[CH:28][C:29]3=[O:35])[C:10]=2[N:9]=[C:8]1[CH3:11])[CH3:17]

참가 물질

7

반응물 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 685335945-[Bis(4-fluorophenyl)methyl]-1-(2-hydroxyethyl)pyridin-2(1h)-oneHCID 86637909ethyl (4-hydroxy-2-methyl-1H-benzimidazol-1-yl)acetate

생성물 1

HCID 131729955Ethyl[4-(2-{5-[bis(4-fluorophenyl)methyl]-2-oxopyridin-1(2h)-yl}ethoxy)-2-methyl-1h-benzimidazol-1-yl]acetate수율 94.4%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of ethyl (4-hydroxy-2-methyl-1H-benzimidazol-1-yl)acetate (476 mg), 5-[bis(4-fluorophenyl)methyl]-1-(2-hydroxyethyl)pyridin-2(1H)-one (694 mg), 1,1′-azobis(N,N-dimethylformamide) (385 mg) and toluene (9.5 mL) was added tributylphosphine (452 mg) at ambient temperature. The mixture was stirred at ambient temperature for 20 hours. The reaction mixture was diluted with a mixture of EtoAc (50 mL) and THF (20 mL), and washed with water (30 mL) and brine (30 mL). The organic layer was dried over anhydrous MgSO4, filtered and evaporated in vacuo to give crude oil. The crude oil was crystallized from solvent(EtOAc and n-hexane) to give ethyl[4-(2-{5-[bis(4-fluorophenyl)methyl]-2-oxopyridin-1(2H)-yl}ethoxy)-2-methyl-1H-benzimidazol-1-yl]acetate (1.07 g) as a white solid.

후처리

  1. washwashed with water (30 mL) and brine (30 mL)
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto give crude oil
  6. customThe crude oil was crystallized from solvent(EtOAc and n-hexane)

출처 및 근거

ORD 기록
ord-1929e57b2c1b460eb7c3ef091f5d99cd
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273745B2

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